Acetone → 5,5-Dimethyl-3-(3-fluorophenyl)-2-hydroxy-4-(4-methylsulfonylphenyl)-2,5-dihydrofuran

HRID 1106579Notes

Reaction equation

[CH3:1][C:2]1([CH3:25])[O:6][C:5](=[O:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:3]1[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1.CC(C[AlH]CC(C)C)C.CC(C)=O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.CO>[CH3:1][C:2]1([CH3:25])[O:6][CH:5]([OH:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:3]1[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a -50° C. solution of 5,5-dimethyl-3-(3-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone (30 g, 83.3 mmol) in 500 mL of THF was added dropwise a solution of DIBAL (90 mL, 1.5 M in toluene) over a period of 15 min. The reaction mixture was allowed to warm to -10° C. over a period of 1 h, then treated with 20 mL of acetone, followed by 50 mL of methanol. The reaction mixture was then warmed to -20° C. and treated with aqueous potassium sodium tartrate (20%, 400 mL). After stirring at r.t. for 1 h, the product was extracted with 500 mL of 2:1 EtOAc/hexane, dried over Na2SO4, filtered and concentrated. The crude product was swished with 2:1 hexane/EtOAc to give 24 g of purified title compound as a white solid.

Workup

temperatureThe reaction mixture was then warmed to -20° C.
extractionthe product was extracted with 500 mL of 2:1 EtOAc/hexane
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give 24 g
customof purified title compound as a white solid

Sources & evidence

ORD record: ord-bb807d0981cc425e904bc278f53c57a5
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057319

Reaction notes

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