Sodium Bicarbonate → 2-(4-Bromophenyl)propane-1,3-diol

HRID 1359962Notes

Reaction equation

HRID 1359962 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:13]=[O:14])[CH:11]=[O:12])=[CH:6][CH:5]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:13][OH:14])[CH2:11][OH:12])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 34946462-(4-Bromophenyl)propanedialHCID 4311764Sodium borohydride

Product 1

HCID 218667012-(4-Bromophenyl)propane-1,3-diolYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (433 mg, 11.5 mmol) was added slowly to a solution of 2.0 g (8.81 mmol) of 2-(4-bromophenyl)malonaldehyde in tetrahydrofuran (20 ml) under ice cooling, and the mixture was stirred for 1.5 hr. A saturated aqueous sodium hydrogencarbonate solution was added thereto. The mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. The solvent was removed by distillation, and the residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:4) to give 1.35 g (yield 66%) of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. customThe solvent was removed by distillation
  4. customthe residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to 1:4)

Sources & evidence

ORD record
ord-4771b3b9cc5d4cb384236d60c4e7047a
Source dataset
uspto-grants-2011_02
Patent number
US07879808B2

Reaction notes

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