Methanol → 2-Hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]-hexadecanoic Acid Methyl Ester

HRID 2106837Notes

Reaction equation

[CH2:1]([CH:7]([C:12](=[O:33])[CH2:13][CH:14]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:8]([O:10][CH3:11])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CO.[BH4-].[Na+]>C1COCC1>[CH2:1]([CH:7]([CH:12]([OH:33])[CH2:13][CH:14]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:8]([O:10][CH3:11])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: -5 °C

Procedure

7.76 g of methyl 2-hexyl-3-oxo-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate (0.017 mol) were dissolved in 500 ml of THF while gassing with argon, treated with 20 ml of MeOH and cooled to -5° C. 5.3 g of sodium borohydride (0.14 mol) were added portionwise while stirring in such a manner that the temperature did not exceed 0° C. After stirring for 3 hours the excess sodium borohydride is filtered off, the reaction mixture was hydrolyzed (to pH 6) with 2N hydrochloric acid in the cold and the solvent was evaporated off. The residue was extracted with ether and the ethereal phase was dried and evaporated. There were obtained 7.71 g of methyl 2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate.

Workup

customdid not exceed 0° C
filtrationis filtered off
customwas evaporated off
extractionThe residue was extracted with ether
customthe ethereal phase was dried
customevaporated

Sources & evidence

ORD record: ord-22cbc1874dee4bd8b81bdb7d6a361eb3
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04931463

Reaction notes

Loading…