Sodium borohydride → methyl delta-hydroxy-2-[5-[(tetrahydro-2H-pyran-2-yl)oxy]-1E,3E-tridecadienyl]benzenepentanoate

HRID 1722341Notes

Reaction equation

[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[CH:18]=[CH:19]/[CH:20]([O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[BH4-].[Na+]>CO>[OH:1][CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[CH:18]=[CH:19]/[CH:20]([O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

To 3 ml of methanol was added 0.1g (0.21 mmol) of the titled product of Example 10. The reaction mixture was cooled to 0°C. and 3mg of NaBH4 was added. After 30 minutes, the reaction was complete. The reaction mixture was quenched with acetone and the volatile components were removed in vacuo. The residue was partitioned between diethyl ether (ether) and water. The organic layer was separated and the aqueous layer was extracted once more with ether and the combined extracts were washed with brine and dried (K2CO3). Removal of the solvent produced 0.11g of a pale yellow oil. The product of this reaction was used without further purification.

Workup

customThe reaction mixture was quenched with acetone
customthe volatile components were removed in vacuo
customThe residue was partitioned between diethyl ether (ether) and water
customThe organic layer was separated
extractionthe aqueous layer was extracted once more with ether
washthe combined extracts were washed with brine
dry with materialdried (K2CO3)
customRemoval of the solvent

Sources & evidence

ORD record: ord-254af94e7df9478d9949b26f625e5dc0
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855324

Reaction notes

Loading…