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

HRID 30855

반응식

HRID 30855 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-02b3ab5fc2254a91a617c8d84fbf65a8
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423156B2

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