Tetrahydrofuran → HCID 10341205, compound

HRID 349725Notes

Reaction equation

[Mg].[Cl:2][C:3]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:4]=1[O:10][CH3:11].[Si](O[CH:20]1[CH2:24][C:23](=[O:25])[C:22]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=2)=[CH:21]1)(C(C)(C)C)(C)C.[O:38]1CCCC1>>[OH:38][CH:24]1[C:23](=[O:25])[C:22]([C:26]2[CH:27]=[C:28]([O:36][CH3:37])[C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=2)=[C:21]([C:7]2[CH:6]=[CH:5][C:4]([O:10][CH3:11])=[C:3]([Cl:2])[CH:8]=2)[CH2:20]1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 30165374-Bromo-2-chloroanisole

HCID 5462224Magnesium

HCID 69110186HCID 69110186, compound

Product 1

HCID 10341205HCID 10341205, compound

Procedure

A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3×35 ml), washed with water (2×20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A)

Workup

customReaction
customwas then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran
customwas removed under reduced pressure
customthe residual reaction mixture
extractionwas extracted with ethyl acetate (3×35 ml)
washwashed with water (2×20 ml)
dry with materialdried over sodium sulfate
concentrationConcentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether)

Sources & evidence

ORD record: ord-a9576572c5124dd0afedcff1b018c3f3
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179937B2

Reaction notes

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