Water → HCID 10225382, compound

HRID 1743228Notes

Reaction equation

C(N(CC)CC)C.[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:21]3[C:22]([CH3:29])=[C:23]([OH:28])[C:24]([CH3:27])=[C:25]([CH3:26])[C:20]=3[O:19][C:18]=2[CH3:30])=[CH:13][CH:12]=1)([CH3:10])[CH3:9].[CH3:31][O:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1.O>C(Cl)(Cl)Cl>[CH3:31][O:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([O:28][C:23]2[C:24]([CH3:27])=[C:25]([CH3:26])[C:20]3[O:19][C:18]([CH3:30])=[C:17]([C:14]4[CH:15]=[CH:16][C:11]([CH:8]([CH3:10])[CH3:9])=[CH:12][CH:13]=4)[C:21]=3[C:22]=2[CH3:29])=[O:38])=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Triethylamine (0.45 mL, 3.21 mmol) was added to a solution of 3-(4-isopropylphenyl)-2,4,6,7-tetramethylbenzofuran-5-ol (0.90 g, 2.92 mmol) and 4-methoxybenzoyl chloride (0.55 g, 3,21 mmol) in chloroform (15 mL) at room temperature, and the mixture was stirred for 3 hours at 60° C. Water (30 mL) was poured into the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with 1 N hydrochloric acid and saturated sodium hydroxide, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from ethanol to obtain the title compound (0.52 g, yield 79).

Workup

extractionwas then extracted twice with ethyl acetate
washwashed with 1 N hydrochloric acid and saturated sodium hydroxide
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was crystallized from ethanol

Sources & evidence

ORD record: ord-9b091b9364d3439a8300eabdb810e2b0
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008950B1

Reaction notes

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