tert-Butanol → 2-(4-Methoxybenzyl)-3-oxopentanoic acid ethyl ester

HRID 1944282Notes

Reaction equation

[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].[C:7](O)([CH3:10])([CH3:9])[CH3:8].[CH2:12]([O:14][C:15](=[O:21])[CH2:16][C:17](=[O:20])[CH2:18][CH3:19])[CH3:13].O1CCC[CH2:23]1>[Cl-].[NH4+]>[CH2:12]([O:14][C:15](=[O:21])[CH:16]([CH2:8][C:7]1[CH:10]=[CH:3][C:2]([O:4][CH3:23])=[CH:1][CH:9]=1)[C:17](=[O:20])[CH2:18][CH3:19])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of potassium tert-butoxide (5.4 g), tetrahydrofuran (80 mL), tert-butanol (0.1 mL) and 3-oxopentanoic acid ethyl ester (5.0 g) at 0° C. was treated with a solution of 1-chloromethyl-4-mothoxybenzene (4.7 mL) in tetrahydrofuran (20 mL), and the resulting mixture was stirred at 0° C. for 30 minutes, and then at room temperature for 24 hours. The mixture was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (1:0 to 0:1 by volume), followed by distillation under reduced pressure (150° C., 1 mbar) gave title compound as a colourless oil (3.0 g). 1H NMR analysis showed that the product existed as a mixture of keto and enol isomers.

Workup

waitat room temperature for 24 hours
extractionextracted with ethyl acetate
dry with materialThe combined extracts were dried over sodium sulfate
customthe solvent removed under reduced pressure
customPurification of the residue by column chromatography on silica gel
washeluting with a mixture of pentane and ethyl acetate (1:0 to 0:1 by volume)
distillationfollowed by distillation under reduced pressure (150° C., 1 mbar)

Sources & evidence

ORD record: ord-c9e5912f3f2e4172a6723c59960bf611
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394830B2

Reaction notes

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