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

HRID 990852

反応式

HRID 990852 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-d08d23b3e47345448ab781cf47449a42
出典データセット
uspto-grants-2002_10
特許番号
US06462055B2

関連ノート

読み込み中…