1-HYDROXYMETHYL-CYCLOPROPANECARBOXYLIC ACID ETHYL ESTER Chemical Properties

Boiling point:

90-94 °C(Press: 8 Torr)

Density 

1.159±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

15.10±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C7H12O3/c1-2-10-6(9)7(5-8)3-4-7/h8H,2-5H2,1H3

InChIKey

PAILVKQSHRJIPE-UHFFFAOYSA-N

SMILES

C1(CO)(C(OCC)=O)CC1

CAS DataBase Reference

3697-68-5

Safety Information

HS Code 

2918199890

1-HYDROXYMETHYL-CYCLOPROPANECARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Uses

Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate acts as a ligand for Suzuki coupling reaction.

Synthesis

Example 64 Preparation of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate A tetrahydrofuran solution of 1 M tri-tert-butoxy lithium aluminum (70.90 mL, 70.90 mmol) was slowly added dropwise to a stirred solution of diethyl cyclopropane-1,1-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL). The reaction system was stirred at 23 °C and gradually warmed to 65 °C and maintained at this temperature for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with 10% sodium bisulfate solution (275 mL) and subsequently extracted with ether. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the light yellow oily target product ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (4.60 g, 91% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.16 (q, J = 7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J = 7, 4 Hz, 2H).

References

[1] Patent: US2012/110702, 2012, A1. Location in patent: Page/Page column 38
[2] Patent: US2013/109566, 2013, A1. Location in patent: Paragraph 0400; 0401
[3] Patent: US2013/288893, 2013, A1. Location in patent: Paragraph 0450-0451
[4] Patent: US2016/60245, 2016, A1. Location in patent: Paragraph 0451; 0452
[5] Patent: US2012/53146, 2012, A1. Location in patent: Paragraph 0170; 0171

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