Water → [3-Chloro-4-(1-hydroxy-ethyl)-phenyl]carbamic acid 2-trimethylsilanyl-ethyl ester

HRID 844302

反応式

HRID 844302 の反応式
[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH2:15])=[C:10]([Cl:16])[CH:9]=1.[BH4-].[Na+].[OH2:22]>O1CCCC1.[OH-].[Na+]>[CH3:19][Si:2]([CH3:1])([CH3:18])[CH2:3][CH2:4][O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:22])[CH3:15])=[C:10]([Cl:16])[CH:9]=1

参加物

6

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18543726(3-Chloro-4-vinyl-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

生成物 1

HCID 54096646[3-Chloro-4-(1-hydroxy-ethyl)-phenyl]carbamic acid 2-trimethylsilanyl-ethyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒2 回

実験手順

(3-Chloro-4-vinyl-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester (2.6 g) is added to a solution of mercuric acetate (3.48 g) in water (7 mL) and tetrahydrofuran (5.25 mL) and the mixture is stirred for approximately 15 hours. 3N Aqueous sodium hydroxide (8.7 mL) and a 0.5 M solution of sodium borohydride in 3N aqueous sodium hydroxide (8.7 mL) are then added and stirring is continued for 6 hours. The solution is then saturated with sodium chloride and extracted with ethyl acetate. These organic extracts are then washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. Following removal of the solvent under reduced pressure the residue is chromatographed over silica gel (20% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a white solid.

後処理

  1. stirringstirring
  2. waitis continued for 6 hours
  3. extractionsaturated with sodium chloride and extracted with ethyl acetate
  4. washThese organic extracts are then washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customremoval of the solvent under reduced pressure the residue
  7. customis chromatographed over silica gel (20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-566e45bd8af842ff820fd3d75d20200e
出典データセット
uspto-grants-2002_04
特許番号
US06380243B1

関連ノート

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