Tetrahydrofuran → tert-Butyl cyclopentylacetate

반응식

[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].C1COCC1.[CH:12]1([CH2:17][C:18](Cl)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]1.[Cl-].[NH4+]>>[CH:12]1([CH2:17][C:18]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

반응물 4

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 3485182Cyclopentylacetyl chloride

HCID 23665647Potassium tert-butoxide

생성물 1

HCID 10797592tert-Butyl cyclopentylacetate

실험 절차

136 ml of a 1 M solution of potassium tert-butoxide in THF (136 mmol) were cooled to 0° C., and 21.0 g (143.2 mmol) of cyclopentylacetic chloride were added dropwise. After the addition had ended, the suspension was warmed to RT and stirred overnight and then added to saturated aqueous ammonium chloride solution. The mixture was extracted three times with diethyl ether. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The desired product was isolated from the residue by kugelrohr distillation (1.6 mbar/160-180° C.). This gave 17.58 g of the target compound (66.6% of theory).