5-Methoxyfuran-2(5H)-one → 4-(2-p-Toluenesulfonyl-prop-2-yl)-5-methoxy-tetrahydrofuran-2-one

HRID 326012

Reaction equation

C([Li])CCC.[CH:6]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:8])[CH3:7].[CH3:19][O:20][CH:21]1[O:25][C:24](=[O:26])[CH:23]=[CH:22]1.P(O)(O)([O-])=O.[Na+]>O1CCCC1.C1CCCCC1>[C:15]1([CH3:18])[CH:14]=[CH:13][C:12]([S:9]([C:6]([CH:22]2[CH:21]([O:20][CH3:19])[O:25][C:24](=[O:26])[CH2:23]2)([CH3:8])[CH3:7])(=[O:10])=[O:11])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -70 °C

Procedure

1.3 ml of a cyclohexane solution of 1.95 M of butyllithium was slowly added with stirring at -70° C. under an inert atmosphere to a mixture of 500 mg of isopropyl-p-tolyl sulfone and 10 ml of anhydrous tetrahydrofuran and the mixture was stirred at -70° C. for 30 minutes. A solution of 287 mg of 5-methoxy-2,5-dihydrofuran-2-one in 4 ml of tetrahydrofuran was added to the mixture over 10 minutes and the mixture was held at -70° C. for one hour and was then poured into aqueous monosodium phosphate solution at 0° C. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was crystallized from isopropyl ether to obtain 490 mg of trans dl 4-(2-p-toluenesulfonyl-prop-2-yl)-5-methoxy-tetrahydrofuran-2-one in the form of white crystals melting at 129° C.

Workup

waitthe mixture was held at -70° C. for one hour
extractionThe mixture was extracted with methylene chloride
washthe organic phase was washed with water
customdried
customevaporated to dryness under reduced pressure
customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record: ord-b53a5e2007d24329b06849f760a07a92
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04443617

Linked notes

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