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

HRID 1367494ノート

反応式

HRID 1367494 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 14009986tert-Butyl 3-oxocyclopentane-1-carboxylate収率 96%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
2 °C

実験手順

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.)+.

後処理

  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

出典と根拠

ORDレコード
ord-cd421189375b431ca283a94321e025c6
出典データセット
uspto-grants-2011_02
特許番号
US07893099B2

反応ノート

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