Water → trans-(Trimethylsilyl)ethyl 2-(4-bromobenzoyl)cyclohexanecarboxylate

HRID 9540

反応式

HRID 9540 の反応式
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[C:14]([OH:16])=[O:15])=[O:7])=[CH:4][CH:3]=1.[CH3:19][Si:20]([CH3:25])([CH3:24])[CH2:21][CH2:22]O.CCN=C=NCCCN(C)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[C:14]([O:16][CH2:22][CH2:21][Si:20]([CH3:25])([CH3:24])[CH3:19])=[O:15])=[O:7])=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 180132-(Trimethylsilyl)ethanolHCID 2725095(1R,2R)-2-(4-bromobenzoyl)cyclohexane-1-carboxylic Acid

生成物 1

HCID 58681290trans-(Trimethylsilyl)ethyl 2-(4-bromobenzoyl)cyclohexanecarboxylate収率 37%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid (5.0 g, 16.07 mmol) in DCM (80 mL) was added 2-(trimethylsilyl)ethanol (2.1 g, 17.68 mmol), N,N′-dimethylamino-pyridine (98 mg, 0.80 mmol), and EDCI (4.0 g, 20.89 mmol). The resulting reaction mixture was stirred at rt for 2 days. Water was added, and the mixture was diluted with DCM. The aqueous layer was separated and extracted with DCM. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane gave trans-(trimethylsilyl)ethyl 2-(4-bromobenzoyl)cyclohexanecarboxylate (2.44 g, 37%). 1H NMR (400 MHz, CD2Cl2) δ −0.01 (s, 9H), 0.85 (m, 2H), 1.45 (m, 3H), 1.73 (m, 2H), 1.90 (m, 2H), 2.18 (m, 1H), 2.71 (m, 1H), 3.80 (m, 1H), 4.05 (m, 2H), 7.58 (d, 2H), 7.70 (d, 2H).

後処理

  1. customThe resulting reaction mixture
  2. customThe aqueous layer was separated
  3. extractionextracted with DCM
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washSilica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane

出典と根拠

ORDレコード
ord-91ac4de46f3e4b839aeb0ff63fe2cf3e
出典データセット
uspto-grants-2006_08
特許番号
US07091228B2

関連ノート

読み込み中…