Hydrochloric Acid → Tert-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-hydroxybutanoate

HRID 249549Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[O:6][CH:5]([CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4](=[O:18])[O:3]1.C(B(CC)CC)C.[BH4-].[Na+].Cl>C1COCC1>[CH3:1][C:2]1([CH3:19])[O:6][CH:5]([CH2:7][CH:8]([OH:17])[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C:4](=[O:18])[O:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (10.88 g, 40.0 mmol) in THF (20 ml), a mixture of THF (96.0 ml) and triethylborane 1M in THF) (56.0 ml) was was added at -78° C. over 45 minutes, followed by stirring at -78° C. for 50 minutes. Thereafter, to the resulting mixture, sodium borohydride (1.51 g, 40.0 mmol) was added in one portion and stirred at -78° C. for 4 hours. After adding 1N hydrochloric acid at 0° C., the mixture was extracted with ethyl acetate and washed with saturated saline. The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to give pure tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-hydroxybutanoate (6.08 g, 22.16 mmol). Yield, 55%.

Workup

additionwas was added at -78° C. over 45 minutes
stirringstirred at -78° C. for 4 hours
extractionthe mixture was extracted with ethyl acetate
washwashed with saturated saline
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-dbd18335da55479099a5686bed46ea32
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05214197

Reaction notes

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