Sodium borohydride → HCID 85700288, compound

HRID 551666Notes

Reaction equation

HRID 551666 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([C:10](=[O:15])[CH2:11][CH2:12][CH:13]=[CH2:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6]>CO>[OH:15][CH:10]([CH2:11][CH2:12][CH:13]=[CH2:14])[CH:4]([CH3:3])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10954205Ethyl 2-methyl-3-oxohept-6-enoate

Product 1

HCID 85700288HCID 85700288, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (2.48 g, 65.7 mmol) was added to a methanol (200 mL) solution of ethyl 2-methyl-3-oxohept-6-enoate (12.1 g, 65.7 mmol) with stirring under ice cooling. The mixture was stirred for 30 minutes in this bath, further stirred at room temperature for 2 hours, and then concentrated under reduced pressure to remove the solvent. The residue was diluted with dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate, and saturated saline, then dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil (6.11 g).

Workup

  1. stirringThe mixture was stirred for 30 minutes in this bath
  2. stirringfurther stirred at room temperature for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent
  5. additionThe residue was diluted with dilute hydrochloric acid
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate, and saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d16866c8f16d4d6e98cb5411a33fb4cf
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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