Sodium hydride → 4-Bromo-2-ethoxyphenethyl 3-cyanophenylcarbamate

HRID 735666ノート

反応式

HRID 735666 の反応式
[H-].[Na+].[N:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10])=[C:4]=[O:5].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[C:17]([O:24][CH2:25][CH3:26])[CH:16]=1>C1COCC1>[C:9]([C:8]1[CH:7]=[C:6]([NH:3][C:4](=[O:5])[O:23][CH2:22][CH2:21][C:18]2[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][C:17]=2[O:24][CH2:25][CH3:26])[CH:13]=[CH:12][CH:11]=1)#[N:10]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27333153-IsocyanatobenzonitrileHCID 578428372-(4-Bromo-2-ethoxyphenyl)ethan-1-ol

生成物 1

HCID 688177644-Bromo-2-ethoxyphenethyl 3-cyanophenylcarbamate収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NaH (346 mg, 8.7 mmol, 60% dispersion in oil) was added in one portion to a solution of 3-isocyanatobenzonitrile (567 mmol, 3.9 mmol) and 62E (960 mg, 3.9 mmol) in THF (40 mL) and the cooling bath was removed. After stirring for 2 h at ambient temperature 1.0 N citric acid (50 mL) was added and the mixture was extracted with diethyl ether. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes) to yield 62F (611 mg, 50%) as a pale, yellow solid. MS (ESI) m/z 411.0/413.0 (M+H)+.

後処理

  1. customthe cooling bath was removed
  2. additionwas added
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-2f00d4618ce74415af3ba3ed1d9f4a62
出典データセット
uspto-grants-2009_09
特許番号
US07592331B2

反応ノート

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