Sodium borohydride → HCID 58338939, compound

HRID 881779Notes

Reaction equation

HRID 881779 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[O:24])[S:5][C:6]=1[C:7]1[S:8][C:9]([C:12]2[S:13][C:14]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[CH3:22])=[CH:15][CH:16]=2)=[CH:10][CH:11]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:23][OH:24])[S:5][C:6]=1[C:7]1[S:8][C:9]([C:12]2[S:13][C:14]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[CH3:22])=[CH:15][CH:16]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58338945HCID 58338945, compound

Product 1

HCID 58338939HCID 58338939, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4MT-CHO (1.35 g, 3.5 mmol) in 30 mL dry ethanol was added 265 mg (7 mmol) sodium borohydride in small portions. The reaction mixture quickly changed color from orange to yellow and the stirring was continued for 30 min. Removal of the solvent under reduced pressure followed by purification with flash silica gel column chromatography using chloroform as eluent yielded yellow crystals (1.32 g, 97.2%).

Workup

  1. customRemoval of the solvent under reduced pressure
  2. customfollowed by purification with flash silica gel column chromatography

Sources & evidence

ORD record
ord-5278763c8e3248ce82722039e2101d7b
Source dataset
uspto-grants-2015_03
Patent number
US08993697B2

Reaction notes

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