Sodium borohydride → 3,5-Bis(dimethylamino)-alpha-[(methylsulfonyl)-methyl]benzyl alcohol

HRID 1413741Notes

Reaction equation

HRID 1413741 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:4]=[C:5]([C:12](=[O:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:6]=[C:7]([N:9]([CH3:11])[CH3:10])[CH:8]=1.[BH4-].[Na+]>C(O)C>[CH3:1][N:2]([CH3:19])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([N:9]([CH3:11])[CH3:10])[CH:8]=1)[CH:12]([OH:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 202903961-[3,5-Bis(dimethylamino)phenyl]-2-(methanesulfonyl)ethan-1-one

Product 1

HCID 541458753,5-Bis(dimethylamino)-alpha-[(methylsulfonyl)-methyl]benzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 7.4 g. of 3',5'-bis(dimethylamino)-2-methylsulfonylacetophenone and 3.8 g. of sodium borohydride in 100 ml. of ethanol was stirred for 20 hours at 25° C. After the addition of 50 ml. of water, the alcohol was removed in vacuo and the remaining aqueous suspension extracted with 400 ml. of ethyl acetate. The ethyl acetate phases were washed with 50 ml. of water, dried over magnesium sulfate and evaporated to dryness in vacuo. Recrystallization of the residue from ethanol gave 3,5-bis(dimethylamino)-α-[(methylsulfonyl)-methyl]benzyl alcohol, having a melting point of 142°-143° C.

Workup

  1. additionA suspension of 7.4 g
  2. additionAfter the addition of 50 ml
  3. customof water, the alcohol was removed in vacuo
  4. extractionthe remaining aqueous suspension extracted with 400 ml
  5. washThe ethyl acetate phases were washed with 50 ml
  6. dry with materialof water, dried over magnesium sulfate
  7. customevaporated to dryness in vacuo
  8. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-942406d787694b039b60d6bdf18b0450
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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