Isopropanol → HCID 13920711, compound

HRID 2291643Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH:5]1[O:9][C:8](=[O:10])[CH:7]=[C:6]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.C(OCC)(=O)C>CC(C)=O.O>[O:10]=[C:8]1[O:9][CH:5]([CH2:4][CH2:3][C:2]([OH:19])=[O:1])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(3-hydroxypropyl)-4-phenyl2(5H)-furanone (90 mg) in acetone (1 ml) was added to a solution of 2N Jones reagent (0.62 ml) in acetone (1 ml) at 0° C. over 10 minutes, and the resulting mixture was stirred at 0° C. for 20 minutes. After addition of isopropyl alcohol (1 ml), the mixture was poured into a mixture of ethyl acetate (20 ml) and water (20 ml). The aqueous layer was separated and extracted with ethyl acetate (10 ml). The organic layers were combined, washed with water and brine succssively, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (3 g) eluting with a mixture of chloroform and methanol (50:1 to 20:1) to give an oily product of 3-(2,5-dihydro5-oxo-3-phenyl-2-furyl)propionic acid, which was crystallized from diethyl ether (60 mg).

Workup

customThe aqueous layer was separated
extractionextracted with ethyl acetate (10 ml)
washwashed with water and brine succssively
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel (3 g)
washeluting with a mixture of chloroform and methanol (50:1 to 20:1)

Sources & evidence

ORD record: ord-08cb65ef430b4511828e960dbd06fc23
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04797417

Reaction notes

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