Diethyl Ether → tert-Butyl 3-oxocyclopentane-1-carboxylate

HRID 1367494노트

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HRID 1367494 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[C:10](O)([CH3:13])([CH3:12])[CH3:11].C(OCC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:10]([O:8][C:7]([CH:4]1[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]1)=[O:9])([CH3:13])([CH3:12])[CH3:11]

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 6386tert-ButanolHCID 2277983-Oxocyclopentanecarboxylic acid

생성물 1

HCID 14009986tert-Butyl 3-oxocyclopentane-1-carboxylate수율 96%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

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온도
2 °C

실험 절차

To a cold (ice bath) solution of 3-oxo-1-cyclopentanecarboxylic acid (1.50 g), tert-butylalcohol (1.05 g) and 4-dimethylaminopyridine (140 mg) in dichloromethane (9 mL) was added a solution of dicyclocarbodiimide in dichloromethane (9 mL). The mixture was stirred 3 hours at ca. 2° C. then diethylether (30 mL) was added and the precipitate was filtered off and discarded. The solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (9:1 v/v) as eluant to afford the title compound (1.80 g, 96%) as colorless oil. MS (EI): 111 (M-OtBu.)+.

후처리

  1. filtrationthe precipitate was filtered off
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (9:1 v/v) as eluant

출처 및 근거

ORD 기록
ord-cd421189375b431ca283a94321e025c6
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893099B2

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