Dichloromethane → 2-(2-{4-[1-(3-Bromo-phenyl)-vinyl]-phenoxy}-ethoxy)-tetrahydro-pyran

HRID 1668732Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.[Br:17][C:18]1[CH:19]=[C:20]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[CH2:25])[CH:21]=[CH:22][CH:23]=1.ClCCl>CN(C)C=O.C1CCCCC1.C(OCC)(=O)C.O>[Br:17][C:18]1[CH:19]=[C:20]([C:24]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:8][CH2:9][O:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)=[CH:30][CH:31]=2)=[CH2:25])[CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Cesium carbonate (4.36 g, 13.4 mmol, 1.2 eq) and 2-(2-bromoethoxy)-tetrahydro-2H-pyran (1.94 mL, 12.8 mmol, 1.2 eq) were added to a solution of 4-[1-(3-bromo-phenyl)-vinyl]-phenol (2.9 g, 10.7 mmol, 1.0 eq) in dry N,N-dimethylformamide (35 mL). The mixture was stirred overnight at 55° C. Dichloromethane (100 mL) and water (50 mL) were then added. The organic phase was washed with water (3×) and dried over sodium sulfate. Evaporation of solvent and purification by flash chromatography (eluent: cyclohexane/ethyl acetate=9:1 then 8:2) gave 2.0 g of desired product as yellow oil (yield 47%).

Workup

washThe organic phase was washed with water (3×)
dry with materialdried over sodium sulfate
customEvaporation of solvent and purification by flash chromatography (eluent

Sources & evidence

ORD record: ord-88d287417cca49baa2fe0f6bf1096c01
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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