Water → tert-Butyl cyclopropanecarboxylate

Temperature

0 °C

To a solution of tert-butanol (9.4 mL, 100 mmol) in 50 mL of anhydrous THF is added under nitrogen during several minutes n-butyl lithium (69 mL, 110 mmol, 1.6 M solution in hexane). After 30 min, the resulting solution is treated by the drop wise addition of a THF solution (40 mL) of cyclopropanecarbonyl chloride (10 mL, 110 mmol). The reaction mixture is further stirred at reflux for 1 h, cooled to 0° C. by an ice bath, and slowly hydrolyzed by the addition of water. The aqueous layer is extracted twice with ether and the combined organic extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by vacuum distillation (bp=70° C., 76 mmHg) to afford the title compound as a yellow oil.

1. temperatureat reflux for 1 h
2. extractionThe aqueous layer is extracted twice with ether
3. dry with materialthe combined organic extracts are dried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. distillationThe residue is purified by vacuum distillation (bp=70° C., 76 mmHg)

ORD record

ord-8b8d300d35a946dd97388d26faeff16d

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07754727B2