1,2-Dichloroethane → 5-Benzyloxy-2-(2-tert-butoxycarbonyl-vinyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

HRID 1181104노트

반응식

HRID 1181104 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:18]=[CH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Si:28]([CH3:33])([CH3:32])[CH2:29][CH2:30]O.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:27][Si:28]([CH3:33])([CH3:32])[CH2:29][CH2:30][O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH:11][C:12]=1[CH:18]=[CH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 180132-(Trimethylsilyl)ethanolHCID 69232261HCID 69232261, 화합물

생성물 1

HCID 692318995-Benzyloxy-2-(2-tert-butoxycarbonyl-vinyl)-benzoic acid 2-trimethylsilanyl-ethyl ester수율 84%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-benzyloxy-2-(2-tert-butoxycarbonyl-vinyl)-benzoic acid (5.50 g, 15.5 mmol) in CH2Cl2 (100 mL) was added 2-trimethylsilyl-ethanol (3.67 g, 31.0 mmol), EDC (5.36 g, 27.9 mmol), and DMAP (3.67 g, 31.0 mmol). The resulting mixture was stirred at room temperature for 12 h, washed with aqueous NH4Cl (150 mL), and extracted with CH2Cl2 (100 mL). The combined organics were dried (Na2SO4) and concentrated. The residue was purified using silica gel chromatography (hexanes/EtOAc 9/1) to afford the title compound as an oil (5.90 g, 84%). 1H NMR (400 MHz, CDCl3): δ 0.07 (s, 9H), 1.14 (t, 2H, J=8.8 Hz), 1.52 (s, 9H), 4.41 (t, 2H, J=8.8 Hz), 5.10 (s, 2H), 6.20 (d, 1H, J=15.6 Hz), 7.13 (dd, 1H, J=3.0, 8.3 Hz), 7.34-7.44 (m, 5H), 7.50 (d, 1H, J=3.0 Hz), 7.53 (d, 1H, J=8.8 Hz), 8.41 (d, 1H, J=16.1 Hz).

후처리

  1. washwashed with aqueous NH4Cl (150 mL)
  2. extractionextracted with CH2Cl2 (100 mL)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified

출처 및 근거

ORD 기록
ord-85ef47600a104190a0c6ae2be9891973
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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