Sodium borohydride → 4-(Ethylamino)-3,5-dimethoxy-alpha-[(methylsulfonyl)-methyl]-benzyl alcohol

HRID 542979Notes

Reaction equation

HRID 542979 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12](=[O:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:6][C:5]=1[O:19][CH3:20])[CH3:2].[BH4-].[Na+]>O>[CH2:1]([NH:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([CH:12]([OH:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:6][C:5]=1[O:19][CH3:20])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 212809514'-(Ethylamino)-3',5'-dimethoxy-2-(methylsulfonyl)acetophenone

Product 1

HCID 541331734-(Ethylamino)-3,5-dimethoxy-alpha-[(methylsulfonyl)-methyl]-benzyl alcohol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 48 g. of 4'-(ethylamino)-3',5'-dimethoxy-2-(methylsulfonyl)acetophenone and 23.8 g. of sodium borohydride in 1 liter of alcohol was stirred at room temperature for 20 hours, resulting in a solution. After the addition of 1 liter of water, the alcohol was evaporated under vacuum. The crystals formed were removed by filtration with suction, washed with water and dried, whereby there was obtained 4-(ethylamino)-3,5-dimethoxy-α-[(methylsulfonyl)-methyl]-benzyl alcohol having a melting point of 121°-122° C.

Workup

  1. additionA suspension of 48 g
  2. customresulting in a solution
  3. customthe alcohol was evaporated under vacuum
  4. customThe crystals formed
  5. customwere removed by filtration with suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-84fb47f0ff084616a91d0e0fa28f761b
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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