Ammonium Chloride → Methyl 3-hydroxy-7,11,15-trimethylhexadeca-6,10,14-trienoate

HRID 488151Notes

Reaction equation

[BH4-].[Na+].[O:3]=[C:4]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:25])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[NH4+].[Cl-]>CO>[OH:3][CH:4]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:25])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Powdered sodium borohydride (38 mg, 1.0 mmol) was added at 0° C. to a stirred solution of methyl 3-oxo-7,11,15-trimethylhexadeca-6,10,14-trienoate (580 mg, 1.8 mmol) in methanol (5 mL) in one portion. The resulting mixture was stirred at 0° C. for 15 minutes, then treated with a saturated aqueous solution of NH4Cl (2 mL). The resulting mixture was extracted with diethyl ether. This extract was washed with water, dried, filtered and evaporated to give the crude product which was purified by flash chromatography. Elution of the column with hexane:ethyl acetate (10:1/v:v) afforded the title compound as a colorless gum.

Workup

extractionThe resulting mixture was extracted with diethyl ether
washThis extract was washed with water
customdried
filtrationfiltered
customevaporated
customto give the crude product which
customwas purified by flash chromatography
washElution of the column with hexane:ethyl acetate (10:1/v:v)

Sources & evidence

ORD record: ord-fba986c2464641bfb52ac3b7c37cf278
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05298655

Reaction notes

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