Sodium borohydride → HCID 58338943, compound

HRID 881781Notes

Reaction equation

HRID 881781 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]2=[N:12][S:13][N:14]=[C:10]2[C:9]([C:15]2[S:19][C:18]([CH:20]=[O:21])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1.[BH4-].[Na+]>C1COCC1.C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]2=[N:12][S:13][N:14]=[C:10]2[C:9]([C:15]2[S:19][C:18]([CH2:20][OH:21])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58338932HCID 58338932, compound

Product 1

HCID 58338943HCID 58338943, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of TBT-CHO (1.4 g, 4.27 mmol) in 80 mL THF and 5 mL dry ethanol was added 163.4 mg (4.3 mmol) sodium borohydride in small portions. The reaction mixture quickly changed color from red to orange and the stirring was continued for 20 min. Removal of the solvent under reduced pressure followed by purification with flash silica gel column chromatography using chloroform as eluent yielded orange crystals (1.4 g, 99.4%).

Workup

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

Sources & evidence

ORD record
ord-182bbccb0bdf43b3a814cf2b30e59aea
Source dataset
uspto-grants-2015_03
Patent number
US08993697B2

Reaction notes

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