Water → tert-Butyl cyclopropanecarboxylate

HRID 1809822Notes

Reaction equation

HRID 1809822 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH:11]1([C:14](Cl)=[O:15])[CH2:13][CH2:12]1.O>C1COCC1>[C:1]([O:5][C:14]([CH:11]1[CH2:13][CH2:12]1)=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 77637Cyclopropanecarbonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 13676038tert-Butyl cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e9518a9e9ca145ffbcf8d25348fe3e07
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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