Methanol → Methyl 3,5-dihydroxy-6,8-decadienoate

HRID 330698Notes

Reaction equation

[OH:1][CH:2]([CH2:8][C:9](=[O:15])[CH:10]=[CH:11][CH:12]=[CH:13][CH3:14])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(B(CC)CC)C.[BH4-].[Na+].CO>C1COCC1>[OH:1][CH:2]([CH2:8][CH:9]([OH:15])[CH:10]=[CH:11][CH:12]=[CH:13][CH3:14])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cold (-15°C.) solution of methyl 3-hydroxy-5-oxo-6,8-decadienoate (18.5 g, 86.9 mmol) in THF (300 mL) was added triethylborane (1M in THF, 113 mL, 113 mmol) and the solution was stirred for 20 minutes. After the mixture was cooled to -78° C., NaBH4 (6 g, 159 mmol) and methanol (37.5 mL) were added. The solution was vigorously stirred for 30 minutes at -78° C. and at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between 1N HCl and ethyl acetate. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (diethyl ether:hexane/3:1) to afford 7.95 g (42.7%) of the title compound as a yellow oil.

Workup

stirringThe solution was vigorously stirred for 30 minutes at -78° C. and at ambient temperature for 3 hours
customThe solvent was removed under reduced pressure
customthe residue was partitioned between 1N HCl and ethyl acetate
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated
customThe residue was purified by chromatography on silica gel (diethyl ether:hexane/3:1)

Sources & evidence

ORD record: ord-aab1b51971874e488b1fae83e7090ea2
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04897490

Reaction notes

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