Sodium borohydride → HCID 53651693, compound

HRID 322968Notes

Reaction equation

HRID 322968 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 543870911,1-Dimethylethyl 3-(3-formylphenyl)-2-propenoate

Product 1

HCID 53651693HCID 53651693, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of tert-butyl 3-(3-formylphenyl)acrylate (5 g) in methanol (150 mL) at 0° C. is treated with sodium borohydride (0.38 g) portionwise. After stirring at 0° C. for 20 minutes the reaction mixture is partitioned between ethyl acetate (200 mL) and water (100 mL). The organic phase is separated, dried over magnesium sulphate and evaporated to give tert-butyl 3-(3-hydroxymethylphenyl)acrylate which is dissolved in dry toluene (50 mL) and treated with tris(triphenylphosphine)rhodium(I) chloride (80 mg) and triethylsilane (8 mL). The mixture is stirred at room temperature for 3 hours, left standing at room temperature for 18 hours and evaporated. The residue is purified by flash chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (4:1 v/v). Fractions homogeneous in the required product are combined and evaporated to give tert-butyl 3-(3-hydroxymethylphenyl)propionate (1.5 g).

Workup

  1. customis partitioned between ethyl acetate (200 mL) and water (100 mL)
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-fccd1719999f416b9647fe0b0c05b975
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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