Diethyl Ether → trans-2-[3-n-Propylsulfonyl-4-(2-bromoethoxy)-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

HRID 982481Notes

Reaction equation

[CH2:1]([S:4]([C:7]1[CH:8]=[C:9]([C@H:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[O:17]2)[CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])(=[O:6])=[O:5])[CH2:2][CH3:3].[Br:33][CH2:34][CH2:35]Br.C([O-])([O-])=O.[K+].[K+].C(OCC)C>CN(C=O)C.O>[CH2:1]([S:4]([C:7]1[CH:8]=[C:9]([C@H:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[O:17]2)[CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[O:13][CH2:35][CH2:34][Br:33])(=[O:6])=[O:5])[CH2:2][CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of trans-2-(3-n-propylsulfonyl-4-hydroxy-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (4.66 g, 10 mmol), 1,2-dibromoethane (1.84 mL, 20.5 mmol) and K2CO3 (4.0 g) in DMF (20 mL) was heated with stirring at 80° C. for 1 h. The reaction mixture was cooled and partioned between ethyl ether and water. The organic layer was separated, dried, and evaporated to a crystalline mass. Recrystallization from ethyl ether-hexane afforded the title compound, mp 135°-136° C.

Workup

temperaturewas heated
temperatureThe reaction mixture was cooled
customThe organic layer was separated
customdried
customevaporated to a crystalline mass
customRecrystallization from ethyl ether-hexane

Sources & evidence

ORD record: ord-c92d4d0a708d474e86977d97f2328341
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04996203

Reaction notes

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