ChemicalBook > Product Catalog > Organic Chemistry > Organometallic compounds > 4-Chloro-2-trimethylstannyl-1-butene
4-Chloro-2-trimethylstannyl-1-butene
4-Chloro-2-trimethylstannyl-1-butene Basic information
- Product Name:
- 4-Chloro-2-trimethylstannyl-1-butene
- Synonyms:
-
- Stannane, (3-chloro-1-methylenepropyl)trimethyl-
- 4-Chloro-2-trimethylstannyl-1-butene
- CAS:
- 85370-32-7
- MF:
- C7H15ClSn
- MW:
- 253.357
- Mol File:
- 85370-32-7.mol
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4-Chloro-2-trimethylstannyl-1-butene Chemical Properties
- form
- liquid
- color
- colorless
- Water Solubility
- insoluble in H2O; soluble in THF, Et2O, CHCl3, and other common organic solvents
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4-Chloro-2-trimethylstannyl-1-butene Usage And Synthesis
Uses
4-Chloro-2-trimethylstannyl-1-butene is a precursor of several bifunctional reagents, which have been employed to effect synthetically useful methylenecyclopentane annulation sequences.
Synthesis
4-chloro-2-trimethylstannyl-1-butene is readily prepared from the commercially available butynol (1). Regioselective addition of Me3SnCu.Me2S (see Trimethylstannylcopper-Dimethyl Sulfide) to (1) provides 3-trimethylstannyl-3-buten-1-ol (2), which upon reaction with Ph3P-CCl4 in the presence of Et3N affords (3) (eq 1). This preparative sequence can be carried out on a reasonably large scale (0.2 mol) and produces overall yields of about 50%.