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

HRID 637525

反応式

HRID 637525 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8078Cyclohexane溶媒

反応条件

温度
-70 °C

実験手順

1.3 ml of a cyclohexane solution of 1.95M 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.

後処理

  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

出典と根拠

ORDレコード
ord-5fdf536d5c014562936f5b020f869c59
出典データセット
uspto-grants-1985_12
特許番号
US04556732

関連ノート

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