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

HRID 1181104ノート

反応式

HRID 1181104 の反応式
[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]

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 180132-(Trimethylsilyl)ethanolHCID 69232261HCID 69232261、化合物

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-85ef47600a104190a0c6ae2be9891973
出典データセット
uspto-grants-2007_10
特許番号
US07282501B2

反応ノート

読み込み中…