Hydrochloric Acid → trans 4-(2-Chloro-prop-2-yl)-5-hydroxy-tetrahydrofuran-2-one

HRID 850907

반응식

HRID 850907 반응식
C1(C)C=CC(S([C:10]([CH3:23])([CH3:22])[CH:11]([CH:17]([O:20]C)[O:18]C)[CH2:12][C:13]([O:15]C)=O)(=O)=O)=CC=1.CCOCC.[Cl-:30].[Li+].Cl>O>[Cl:30][C:10]([C@H:11]1[C@H:17]([OH:18])[O:20][C:13](=[O:15])[CH2:12]1)([CH3:22])[CH3:23]

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 3283Diethyl EtherHCID 433294Lithium ChlorideHCID 12850320Methyl 4-p-tolylsulfonyl-4-methyl-3-dimethoxymethylpentanoate

생성물 1

HCID 12882418trans 4-(2-Chloro-prop-2-yl)-5-hydroxy-tetrahydrofuran-2-one수율 109.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1 g of the product of Example 2, 25 ml of ether and 1 g of dry lithium chloride was stirred under a current of gaseous hydrogen chloride at -30° C. for 2 hours and then at 0° C. for 2 hours after which the current of gaseous hydrogen chloride was stopped. The mixture was stirred at room temperature for 48 hours and after 54 hours of contact, the mixture was poured into iced water. The mixture was extracted with benzene and the organic phase was dried and evaporated to dryness under reduced pressure. The 1.1 g of residue was chromatographed over silica gel and was eluted with a 1-1 benzene-ethyl acetate mixture to obtain 545 mg of dl trans 4-(2-chloro-prop-2-yl)-5-hydroxy-tetrahydrofuran-2-one in the form of crystals melting at 80° C.

후처리

  1. extractionThe mixture was extracted with benzene
  2. customthe organic phase was dried
  3. customevaporated to dryness under reduced pressure
  4. customThe 1.1 g of residue was chromatographed over silica gel
  5. washwas eluted with a 1-1 benzene-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-f478c52a4cc440aa81e8c7f737a8accb
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382037

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