(R)-(-)-Benzyl glycidyl ether Chemical Properties

Melting point:

88-93°C

Boiling point:

130 °C (0.1 mmHg)

alpha 

-5.4 º (c=5 in toluene)

Density 

1.077 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.517(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

paste (yellow)

Specific Gravity

1.077

color 

Colorless to Almost colorless

optical activity

[α]20/D 5.4°, c = 5 in toluene

Water Solubility 

Soluble in water.

BRN 

3588399

InChI

InChI=1S/C10H12O2/c1-2-4-9(5-3-1)6-11-7-10-8-12-10/h1-5,10H,6-8H2/t10-/m0/s1

InChIKey

QNYBOILAKBSWFG-JTQLQIEISA-N

SMILES

O1C[C@@H]1COCC1=CC=CC=C1

CAS DataBase Reference

14618-80-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

RTECS 

TX2860020

HS Code 

29109000

Toxicity

mic-sat 660 nmol/plate MUREAV 298,197,1993

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(R)-(-)-Benzyl glycidyl ether Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

Used in the preparation of the lactone fragment of compactin and mevinolin. Chiron in the preparation of syn-1,3-polyols, dideoxynucleosides, and a spiroacetal cyanohydrin.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 4807, 1980 DOI: 10.1016/0040-4039(80)80145-6

General Description

1H-Pyrazol-3-ylboronic acid hydrate can be used as a reactant in the Suzuki-Miyaura coupling reaction to synthesize pyrazole derivatives by reacting with different aryl halides over the palladium catalyst.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Synthesis

NaH (179 mg, 4.10 mmol, 55% oil solution) was suspended in THF (2 mL) and cooled to 0 °C under argon protection. A THF solution (4 mL) of (S)-oxiran-2-ylmethanol (S1, 200 mg, 2.70 mmol) and benzyl bromide (0.340 mL, 2.86 mmol) were added sequentially. The reaction mixture was heated and stirred at reflux for 19 hours. After completion of the reaction, the reaction was quenched with 0.1 M phosphate buffer (pH 6.5). The product was extracted with ethyl acetate (3×) and the organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by fast column chromatography on silica gel (eluent: hexane/ethyl acetate = 10/1) to afford (R)-benzyloxymethylepoxane (S21) as a colorless oil (196 mg, 44%).1H NMR (300 MHz, CDCl3) δ = 2.62 (dd, J1 = 2.5 Hz, J2 = 5.0 Hz, 1H), 2.80 (dd, J1 = 3.0 Hz, J2 = 5.0 Hz, 1H), 3.19 (dd, J1 = 2.5 Hz, J2 = J3 = 3.0 Hz, J4 = 5.5 Hz, 1H), 3.44 (dd, J1 = 5.5 Hz, J2 = 11.5 Hz, 1H), 3.77 (dd, J1 = 3.0 Hz, J2 = 11.5 Hz, 1H), 4.57 (d, J = 12.0 Hz, 1H), 4.61 (d, J = 12.0 Hz, 1H), 7.25-7.38 (m, 5H); 13C NMR (75 MHz, CDCl3) δ = 44.3, 50.8, 70.8, 73.3, 127.7, 128.4, 137.8; HRMS (EI) m/z 164.0825 (calculated for C10H12O2, M+ 164.0837).

Purification Methods

This ether in EtOAc is dried (Na2SO4), then purified by flash chromatography using pet ether/EtOAc (5:1) as eluent. The ether distils through a short path distillation apparatus (Kügelrohr) as a colourless liquid. Alternatively, dissolve it in CHCl3, wash it with H2O, dry (Na2SO4), evaporate and purify by silica gel chromatography. [Anisuzzamen & Owen J Chem Soc 1021 1967, Takano et al. Heterocycles 1 6 381 1981, Lipshutz et al. Org Synth 69 82 1990, Takano et al. Synthesis 539 1989, Honda et al. Chem Pharm Bull Jpn 39 1385 1991, Beilstein 12 IV 2277.]

References

[1] Collection of Czechoslovak Chemical Communications, 2009, vol. 74, # 5, p. 651 - 769
[2] Chemistry - A European Journal, 2010, vol. 16, # 47, p. 14074 - 14082
[3] Tetrahedron, 2002, vol. 58, # 25, p. 5109 - 5117
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 663 - 677
[5] European Journal of Organic Chemistry, 2005, # 22, p. 4773 - 4788

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