Water → ethyl 5-{(2RS,3SR)-3-hydroxy-2-(4-nitrophenyl)butyl}-2-furancarboxylate

HRID 1602573Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:22](=[O:24])[CH3:23])[CH2:11][C:12]2[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].O>O1CCCC1>[OH:24][CH:22]([CH3:23])[CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH2:11][C:12]1[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

5.48 g of ethyl 5-{2-(4-nitrophenyl)-3-oxobutyl}-2-furancarboxylate in 50 ml of tetrahydrofuran was mixed with 16.5 ml of 1M lithium tri-sec-butylborohydride in tetrahydrofuran under cooling at -78° C. under stirring and stirred at the same temperature for 2 hours. After addition of water, the reaction solution was stirred at room temperature for 1 hour and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1→1/1] to give 3.66 g of the title compound as a pale yellow oily substance.

Workup

stirringstirred at the same temperature for 2 hours
stirringthe reaction solution was stirred at room temperature for 1 hour
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationThe desiccant was filtered off
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1→1/1]

Sources & evidence

ORD record: ord-3df4e80ae07c4f96bb58a74ad991b59d
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981573

Reaction notes

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