Potassium Carbonate → HCID 18766428, compound

HRID 480699Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[C:19]([CH3:28])([CH3:27])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C)C=O>[CH3:8][O:7][C:5]([C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][CH:9]=1)[O:1][C:19]([CH3:28])([CH3:27])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 3-hydroxybenzoate (17.05 g, 0.112 mol) was dissolved in dimethylformamide (100 mL). Subsequently, potassium carbonate (20.12 g, 0.145 mol) and then tert-butyl 2-bromoisobutyrate (50.00 g, 0.224 mol) were added thereto, and the mixture was stirred overnight at 80° C. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the concentrate. Washing was performed sequentially with water and saturated brine, followed by drying over sodium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby a colorless oil was obtained (17.03 g, 57.80 mmol, 51.6%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
additionwas added to the concentrate
washWashing
dry with materialby drying over sodium sulfate
filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby a colorless oil
customwas obtained (17.03 g, 57.80 mmol, 51.6%)

Sources & evidence

ORD record: ord-874024310be54d0090d73c4cd02b471f
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653334B1

Reaction notes

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