Acetic Anhydride → Tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate

HRID 643541ノート

反応式

HRID 643541 の反応式
[OH:1][CH:2]([C:4]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7][C:6]([O:11][CH3:12])([O:9][CH3:10])[CH2:5]1)[CH3:3].C(N(CC)CC)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:27]([O:1][CH:2]([C:4]1([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8][CH2:7][C:6]([O:11][CH3:12])([O:9][CH3:10])[CH2:5]1)[CH3:3])(=[O:29])[CH3:28]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57880496Tert-butyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclopentanecarboxylate

生成物 1

HCID 68534118Tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate

試薬・触媒・溶媒 2

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

実験手順

A solution of tert-butyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclopentanecarboxylate (8.64 g, 31.5 mmol) in 100 mL of DCM was treated with triethylamine (8.78 mL, 63.0 mmol) followed by acetic anhydride (5.94 mL, 63.0 mmol). Then DMAP (˜200 mg) was added and the resulting mixture was stirred at rt overnight. The reaction mixture was diluted with DCM, washed twice with 1N HCl solution, once with saturated NaHCO3 solution, and once with brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by flash chromatography (silica, 20% ethyl acetate/hexanes) provided tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate.

後処理

  1. washwashed twice with 1N HCl solution, once with saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (silica, 20% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-5ce2ad3d85954e69a9b8fd82cb956518
出典データセット
uspto-grants-2010_04
特許番号
US07700591B2

反応ノート

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