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

HRID 480707Notes

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 (7.63 g, 50.10 mmol), potassium carbonate (13.85 g, 100.3 mmol), and tert-butyl 2-bromoisobutyrate (30.37 g, 100.3 mmol) were dissolved in dimethylformamide (9 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, followed by washing sequentially with water and saturated brine. The mixture was subjected to drying over magnesium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound was obtained (3.55 g, 10.62 mmol, 21.2%).

Workup

extractionthe resultant mixture was extracted with diethyl ether
washby washing sequentially with water and saturated brine
dry with materialto drying over magnesium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound
customwas obtained (3.55 g, 10.62 mmol, 21.2%)

Sources & evidence

ORD record: ord-2fd2fdc7173b476bb8e81673fd6cff8c
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653334B1

Reaction notes

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