Water → (Z)-5-Acetylamino-2,4,6,7-tetramethyl-2-styryl-2,3-dihydrobenzofuran

HRID 2260675Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])CCC.[C:12]([NH:15][C:16]1[C:17]([CH3:30])=[C:18]([CH3:29])[C:19]2[O:23][C:22]([CH:25]=O)([CH3:24])[CH2:21][C:20]=2[C:27]=1[CH3:28])(=[O:14])[CH3:13].O>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:12]([NH:15][C:16]1[C:17]([CH3:30])=[C:18]([CH3:29])[C:19]2[O:23][C:22]([CH3:24])(/[CH:25]=[CH:7]\[C:3]3[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=3)[CH2:21][C:20]=2[C:27]=1[CH3:28])(=[O:14])[CH3:13]

Participants

Conditions

Temperature: -20 °C

Procedure

A suspension of benzyltriphenylphosphonium chloride (0.7 g, 1.8 mmol) in tetrahydrofuran (10 ml) was cooled to -20° C. and n-butyllithium hexane solution (1.6 M, 1.12 ml, 1.8 mmol) was added dropwise. The reaction mixture was stirred for 30 minutes and then a solution of 5-acetylamino-2-formyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (0.45 g, 1.7 mmol) in tetrahydrofuran (5 ml) was added. The reaction mixture was stirred at room temperature for additional 30 minutes. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The extract was washed with water, dried and then concentrated. The residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1) to obtain the desired compound (0.44 g, yield: 76.2%) as oil.

Workup

stirringThe reaction mixture was stirred at room temperature for additional 30 minutes
extractionthe product was extracted with ethyl acetate
washThe extract was washed with water
customdried
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1)

Sources & evidence

ORD record: ord-32a609b450604146bd1a44dae91e11f1
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478844

Reaction notes

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