Dimethyl Sulfoxide → 2-Formyl-3-benzyloxy-6-methyl-pyran-4(1H)-one

HRID 1279417Notes

Reaction equation

[OH:1][CH2:2][C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CS(C)=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:2]([C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:1]

Participants

Conditions

Temperature: 4 °C

Procedure

To a solution of 2-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one (5.28 g, 21.5 mmol, 1 eq) in 100 ml chloroform was added 27 ml of dimethyl sulfoxide and 18.5 ml of triethylamine and the reaction mixture was cooled with an ice-bath to an internal temperature of 3-5° C. Then sulfur trioxide pyridine complex (17.1 g 107 mmol, 5 eq) was added and the mixture was allowed to thaw to room temperature. After stirring for overnight at room temperature, the reaction mixture was washed with water (2×50 ml) and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo to yield an organe oil. Further purification by column chromatography on silica gel (eluant: Et2O) furnished the pure product (4.6 g, 87.7%) as a white crystalline solid. m.p. 78-81° C.

Workup

additionThen sulfur trioxide pyridine complex (17.1 g 107 mmol, 5 eq) was added
customthaw to room temperature
washthe reaction mixture was washed with water (2×50 ml)
dry with materialthe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto yield an organe oil
customFurther purification by column chromatography on silica gel (eluant: Et2O)

Sources & evidence

ORD record: ord-a50e998f4b844593a593720baba50c65
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448273B1

Reaction notes

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