Sodium borohydride → 4-(1-Hydroxymethyl-heptyl)-benzoic acid methyl ester

HRID 658307Notes

Reaction equation

HRID 658307 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:17]=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:17][OH:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866258334-(1-Formyl-heptyl)-benzoic acid methyl ester

Product 1

HCID 674861584-(1-Hydroxymethyl-heptyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(1-Formyl-heptyl)-benzoic acid methyl ester (3.17 g, 12.1 mmol) is dissolved in ethanol (50 mL) and allowed to stir under nitrogen in an ice bath at 0° C. Sodium borohydride (0.457 g, 12.1 mmol) is added to the mixture in one portion. The reaction is allowed to stir at 0° C. for one hour, then warmed slowly to room temperature for several hours and is monitored by TLC. Upon complete consumption of starting material, the reaction is carefully quenched with water and the ethanol is removed in vacuo. The remaining mixture is diluted with ethyl acetate. The two phases are separated, and the organic layer washed, dried, and concentrated. The title compound is used in the next step without further purification. MS (ES): 265.2 [M+H]+.

Workup

  1. stirringto stir at 0° C. for one hour
  2. temperaturewarmed slowly to room temperature for several hours
  3. customUpon complete consumption of starting material
  4. customthe reaction is carefully quenched with water
  5. customthe ethanol is removed in vacuo
  6. additionThe remaining mixture is diluted with ethyl acetate
  7. customThe two phases are separated
  8. washthe organic layer washed
  9. customdried
  10. concentrationconcentrated
  11. customThe title compound is used in the next step without further purification

Sources & evidence

ORD record
ord-c9cb90b95655470f95d38a58a967bbc7
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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