tert-Butyl acetate → t-Butyl (S)-5-benzyloxy-3-oxononanoate

HRID 2289380Notes

Reaction equation

[C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])(=[O:3])[CH3:2].[CH2:9]([O:16][C@@H:17]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][C:19](OC)=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1>[CH2:9]([O:16][C@@H:17]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][C:19](=[O:20])[CH2:2][C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 48.7 g of t-butyl acetate in 50 ml of dried THF was then added dropwise to the solution from a dropping funnel at the same temperature over 30 minutes, followed by stirring for 45 minutes. The resulting reaction mixture was further cooled to -50° C., and a solution of 45.4 g of methyl (S)-3-benzyloxyheptanoate in 50 ml of dried THF was added thereto over 30 minutes, followed by stirring for 2 hours while maintaining at that temperature. The reaction mixture was poured into a saturated ammonium chloride aqueous solution and extracted with diethyl ether. The extract was washed with a sodium chloride aqueous solution, and the solvent was removed by distillation under reduced pressure to obtain 67 g of a crude product, which was then purified by silica gel column chromatography to obtain 36 g (53.3%) of the titled compound.

Workup

customThe resulting reaction mixture
waitover 30 minutes
stirringby stirring for 2 hours
temperaturewhile maintaining at that temperature
extractionextracted with diethyl ether
washThe extract was washed with a sodium chloride aqueous solution
customthe solvent was removed by distillation under reduced pressure
customto obtain 67 g of a crude product, which
customwas then purified by silica gel column chromatography

Sources & evidence

ORD record: ord-3b84c6c9095c41d0882e1a96150c6123
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093345

Reaction notes

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