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

HRID 1385150Notes

Reaction equation

HRID 1385150 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-a9d173edcc484b7db811fcd6a6f6a8b2
Source dataset
uspto-grants-2001_07
Patent number
US06262082B1

Reaction notes

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