Potassium Carbonate → HCID 9804934, compound

HRID 1841290Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([O:15][CH2:16][CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Br[CH2:19][CH:20]=[C:21]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH2:25][O:24][C:23]2[CH:33]=[CH:34][CH:35]=[CH:36][C:22]1=2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1C=CC=CC=1>[CH:29]1[C:28]2[C:21](=[CH:20][CH2:19][O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([O:15][CH2:16][CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=3)[C:22]3[CH:36]=[CH:35][CH:34]=[CH:33][C:23]=3[O:24][CH2:25][O:26][C:27]=2[CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 3-(4-hydroxyphenyl)-2-ethoxypropionate (0.96 g, 4.0 mmol), 12-(2-bromoethylidene)-12H-dibenzo[d,g]-1,3-dioxocine (1.07 g, 3.3 mmol) and potassium carbonate (0.45 g, 4.5 mmol) in dimethylformamide (15 ml) was heated to 60° C. for 8.5 h. The reaction mixture was diluted with benzene (50 ml), washed with water (2×20 ml), dried (MgSO4) and evaporated. The residue (1.95 g) was purified by column chromatography on silica gel (benzene and benzenelethyl acetate (9:1) eluents). The benzene fractions were discarded, whilst the benzene/ethyl acetate fractions were evaporated to give the title compound as an oil: 0.97 g (62%).

Workup

washwashed with water (2×20 ml)
dry with materialdried (MgSO4)
customevaporated
customThe residue (1.95 g) was purified by column chromatography on silica gel (benzene and benzenelethyl acetate (9:1) eluents)
customwere evaporated

Sources & evidence

ORD record: ord-147ce69ee54044fbb8740a693937c29d
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683111B2

Reaction notes

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