Water → tert-Butyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

HRID 480686Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:22]([CH3:31])([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O>CN(C)C=O>[CH2:12]([O:11][C:9]([CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][C:22]([CH3:31])([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:10])[CH:13]=[CH2:14]

Participants

Conditions

Temperature: 80 °C

Procedure

Allyl 3-hydroxyphenylacetate (2.64 g, 13.7 mmol), potassium carbonate (3.79 g, 27.4 mmol), and tert-butyl 2-bromoisobutyrate (7.65 g, 34.3 mmol) were dissolved in dimethylformamide (5 mL), and the mixture was stirred for 13 hours at 80° C. The reaction mixture was added to water, and the resultant mixture was extracted with diethyl ether. Washing was performed sequentially with water and saturated brine, followed by drying over magnesium sulfate. The mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound was obtained (3.47 g, 10.38 mmol, 75.7%).

Workup

extractionthe resultant mixture was extracted with diethyl ether
washWashing
dry with materialby drying over magnesium sulfate
concentrationThe mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound
customwas obtained (3.47 g, 10.38 mmol, 75.7%)

Sources & evidence

ORD record: ord-e4bb55fcf7314091838a119632fd7785
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653334B1

Reaction notes

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