Hydrochloric Acid → (2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methanol

HRID 1877035

Reaction equation

[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]=[O:8].Br[Mg][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(OCC)C.Cl.O>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]([CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[OH:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-methyl-5-phenylfuran-3-carbaldehyde (1.9 g) in tetrahydrofuran (30 mL) was added dropwise bromo(tetrahydro-2H-pyran-4-yl)magnesium-diethyl ether solution (30 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 30 min. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (10% ethyl acetate/hexane to 40% ethyl acetate/hexane) to give the title compound (2.3 g, 86%) as an oil.

Workup

additionafter the completion of the dropwise addition
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column (10% ethyl acetate/hexane to 40% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-9ee7c736d71249d8b6d97a2b035b8719
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309580B2

Linked notes

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