Ethanol → HCID 54487090, compound

HRID 542954Notes

Reaction equation

HRID 542954 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:16](=[O:22])[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:6]=[C:7]([O:14][CH3:15])[C:8]=1[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.C(O)C.[BH4-].[Na+].[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:14][CH3:15])[C:8]=1[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[CH:16]([OH:22])[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21281011HCID 21281011, compound

Product 1

HCID 54487090HCID 54487090, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 1.54 g. of 3',5'-dimethoxy-2-(methylsulfonyl)-4'-(pyrrol-1-yl)-acetophenone in 20 ml. of ethanol and 20 ml. of water was treated with a solution of 0.4 g. of sodium borohydride in 5 ml. of water with addition of 0.1 g. of sodium hydroxide. The mixture was stirred at room temperature for an additional 3 hours, cooled with ice, diluted with 50 ml. of water and filtered under vacuum. After recrystallization from ethanol, there was obtained 3,5-dimethoxy-α-[(methylsulfonyl)-methyl]-4-(pyrrol-1-yl)-benzyl alcohol having a melting point of 192° C.

Workup

  1. additionA suspension of 1.54 g
  2. temperaturecooled with ice
  3. additiondiluted with 50 ml
  4. filtrationof water and filtered under vacuum
  5. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-4a85c2f357b84ac3927911681b8fa4af
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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