Potassium Carbonate → HCID 54009290, compound

HRID 1278831Notes

Reaction equation

HRID 1278831 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[O:17][C:16]=3[CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([CH2:23][CH3:24])[C:3]=1[OH:25].[H-].[Na+].Br[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH3:35][O:34][C:32](=[O:33])[CH2:31][CH2:30][CH2:29][O:25][C:3]1[C:4]([CH2:23][CH3:24])=[CH:5][C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[O:17][C:16]=3[CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)=[CH:7][C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 107604Methyl 4-bromobutyrate2×HCID 101787952-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenol

Product 1

HCID 54009290HCID 54009290, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenol (0.30 g, 0.76 mmol), 60% sodium hydride (33 mg, 0.83 mmol), 4-bromobutyric acid, methyl ester (0.44 mL, 3.82 mmol), and anhydrous benzene (1.0 mL) was heated at 100° for 6 h. A second portion of 4-bromobutyric acid methyl ester (0.45 mL, 3.91 mmol) and potassium carbonate (0.5 g, 3.62 mmol) was added and the reaction mixture was heated at 100° for 6 h. The crude reaction mixture was chromatographed with hexane/ethyl acetate to give the title compound as a solid (0.31 g, 82%): NMR (DMSO-d6): δ 8.00 (d, J=8 Hz, 1H), 7.98 (s, 1H), 7.48 (d,-J=8 Hz, 1H), 7.46 (d, J=2 Hz, 1H), 7.43 (ddd, J=1, 7, 8 Hz, 1H), 7.35 (ddd, J=1, 7, 8 Hz, 1H), 7.26 (d, J=2 Hz, 1H), 4.03 (dd, J=6, 9 Hz, 1H), 3.98 (dd, J=6, 9 Hz, 1H), 3.63 (s, 3H), 2.74 (d of quartets, J=7, 15 Hz, 1H), 2.69 (d of quartets, J=7, 15 Hz, 1H), 2.62 (t, J=7 Hz, 2H), 2.38 (s, 3H), 2.09 (quintet, J=7 Hz, 2H), 1.56 (s, 3H), 1.18 (t, J=7 Hz, 3H); MS(EI): [M+], 1 bromine isotope pattern, 494/496.

Workup

  1. temperaturethe reaction mixture was heated at 100° for 6 h
  2. customThe crude reaction mixture
  3. customwas chromatographed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-86d21c832d1b49d082b8828ab5c94cc7
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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