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

HRID 326012

반응식

HRID 326012 반응식
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

참가 물질

7

반응물 4

HCID 1120425-Methoxyfuran-2(5H)-oneHCID 8167921-(Isopropylsulfonyl)-4-methylbenzeneHCID 23672064Monosodium phosphateHCID 178418339Butyllithium

생성물 1

HCID 128824134-(2-p-Toluenesulfonyl-prop-2-yl)-5-methoxy-tetrahydrofuran-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b53a5e2007d24329b06849f760a07a92
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04443617

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