Ethanol → HCID 21280981, compound

HRID 542958Notes

Reaction equation

HRID 542958 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]([C:15](=[O:21])[CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=[C:11]([O:22][CH2:23][CH:24]=[CH2:25])[C:6]=1[NH:7][C:8](=[O:10])[CH3:9])[CH:2]=[CH2:3].C(O)C.[BH4-].[Na+].[OH-].[Na+]>O>[CH2:1]([O:4][C:5]1[CH:14]=[C:13]([CH:15]([OH:21])[CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=[C:11]([O:22][CH2:23][CH:24]=[CH2:25])[C:6]=1[NH:7][C:8](=[O:10])[CH3:9])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21280995HCID 21280995, compound

Product 1

HCID 21280981HCID 21280981, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 1.7 g. of 2',6'-bis(allyloxy)-4'-[(methylsulfonyl)-acetyl]acetanilide in 20 ml. of ethanol and 20 ml. of water was treated with a solution of 0.40 g. of sodium borohydride in 5 ml. of water. There was also added 0.1 g. of sodium hydroxide. The mixture was stirred for 3 hours at room temperature and evaporated to dryness. The residue was taken up in water, removed by filtration under vacuum, dried and recrystallized from ethyl acetate/petroleum ether, whereby there was obtained 2',6'-bis(allyloxy)-4'-[1-hydroxy-2-(methylsulfonyl)-ethyl]-acetanilide having a melting point of 162° C.

Workup

  1. additionA suspension of 1.7 g
  2. customevaporated to dryness
  3. customremoved by filtration under vacuum
  4. customdried
  5. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-c133e765068e489ba8796dec79561f3c
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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