Vinyl Acetate → HCID 59557768、化合物

HRID 2038520ノート

反応式

HRID 2038520 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:24](OC=C)(=O)[CH3:25]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][O:15][CH:24]=[CH2:25])=[CH:10][CH:9]=2)[CH:16]=1

参加物

6

反応物 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 59557735HCID 59557735、化合物

生成物 1

HCID 59557768HCID 59557768、化合物収率 67.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of (4-(5-bromo-2-chlorobenzyl)phenyl)methanol (intermediate AK) (1.5 g, 4.81 mmol), [IrCl(cod)]2 (31 mg, 0.046 mmol) and sodium carbonate (0.29 g, 2.73 mmol) in toluene (6 mL) was added vinyl acetate (0.84 mL, 9.10 mmol) under argon. The reaction mixture was heated to 100° C. and stirred for 4 h. The solution was allowed to cool to room temperature, and then diluted with 50 mL of ethyl acetate. The mixture was washed with water (20 mL) and then with brine (20 mL), and dried over sodium sulfate. The residue was concentrated and purified by column chromatography (eluent EA:PE:Et3N=1:30:0.01) to provide 1.09 g of white solid. 1H NMR (CDCl3, 400 MHz): δ 7.36˜7.28 (m, 5H), 7.22 (d, 2H), 6.61 (dd, J=14.4 and 6.8 Hz, 1H), 4.78 (s, 2H), 4.37˜4.33 (dd, J=14.4 and 2.4 Hz, 1H), 4.14˜4.12 (dd, J=6.8 and 2.4 Hz, 1H), 4.09 (s, 2H).

後処理

  1. temperatureto cool to room temperature
  2. washThe mixture was washed with water (20 mL)
  3. dry with materialwith brine (20 mL), and dried over sodium sulfate
  4. concentrationThe residue was concentrated
  5. custompurified by column chromatography (eluent EA:PE:Et3N=1:30:0.01)

出典と根拠

ORDレコード
ord-ec7a3302ed684fadbc732743a3597828
出典データセット
uspto-grants-2013_11
特許番号
US08575321B2

反応ノート

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