Sodium borohydride → Methyl 2-(1-hydroxyethyl)-6-heptenoate

HRID 890703Notes

Reaction equation

HRID 890703 reaction equation
[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:5]([O:7][CH3:8])=[O:6])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10487736Methyl 2-acetyl-6-heptenoate

Product 1

HCID 22245821Methyl 2-(1-hydroxyethyl)-6-heptenoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.00 g (27.1 mmol) of methyl 2-acetyl-6-heptenoate (Example 20A) are introduced into 50 ml of methanol and ice-cooled. 0.56 g (14.9 mmol) of sodium borohydride are added in portions and the mixture is stirred for a further 1 h. The batch is then evacuated from the solvent, taken up in diethyl ether and washed with 1 N hydrochloric acid. The organic phase is dried, concentrated and flash-chromatographed using the eluent petroleum ether/ethyl acetate 10/1.

Workup

  1. temperaturecooled
  2. customThe batch is then evacuated from the solvent
  3. washwashed with 1 N hydrochloric acid
  4. customThe organic phase is dried
  5. concentrationconcentrated
  6. customflash-chromatographed

Sources & evidence

ORD record
ord-8bbd0b3fe44441efa4c8b28354330b78
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

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