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

HRID 1940125
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HRID 1940125 반응식
[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
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참가 물질

7

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HCID 180AcetoneHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 99068925,5-dimethyl-3-(3-fluorophenyl)-4-(4-methylsulfonyl)phenyl-2(5H)-furanone

생성물 1

HCID 98637875,5-Dimethyl-3-(3-fluorophenyl)-2-hydroxy-4-(4-methylsulfonylphenyl)-2,5-dihydrofuran

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

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, 1.5M 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.

후처리

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

출처 및 근거

ORD 기록
ord-35ecf164f8324fa09fc7b7088959472d
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05698584

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