Dimethyl oxalate → Methyl 4-hydroxy-alpha-oxo-6H-thieno[2,3-b]-thiopyran-5-acetate

HRID 372742노트

반응식

HRID 372742 반응식
C[O-].[Na+].CO[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8].[S:12]1[C:16]2[S:17][CH2:18][CH2:19][C:20](=[O:21])[C:15]=2[CH:14]=[CH:13]1>C1C=CC=CC=1>[OH:21][C:20]1[C:15]2[CH:14]=[CH:13][S:12][C:16]=2[S:17][CH2:18][C:19]=1[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 11120Dimethyl oxalateHCID 10942334Sodium MethoxideHCID 110302745,6-Dihydro-4H-thieno[2,3-b]thiopyran-4-one

생성물 1

HCID 22751985Methyl 4-hydroxy-alpha-oxo-6H-thieno[2,3-b]-thiopyran-5-acetate수율 91%

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

A mixture of sodium methoxide (21.6 g, 0.4 mole) and dimethyloxalate (47.2 g, 0.4 mole) in benzene (300 ml) is refluxed for 5 min. in order to dissolve most of the solid. To the cooled solution is added a solution of 5,6-dihydro-4H-thieno[2,3-b]-thiopyran-4-one (34 g, 0.2 mole) in benzene (300 ml) and the mixture is stirred for 3 hrs. to give a yellow suspension. The mixture is poured into ice-water mixture (1750 ml). After separating the aqueous layer from the benzene layer, the benzene layer is extracted with 1(N) NaOH solution (250 ml), and the combined aqueous solution is washed once with ether (100 ml) and acidified with (N) HCl. The yellow crystalline glyoxalate is filtered off and dried over P2O5 to give 45.8 g (91%) of the desired product; m.p. 53°-56° C.

후처리

  1. temperatureis refluxed for 5 min. in order
  2. dissolutionto dissolve most of the solid
  3. customto give a yellow suspension
  4. customAfter separating the aqueous layer from the benzene layer
  5. extractionthe benzene layer is extracted with 1(N) NaOH solution (250 ml)
  6. washthe combined aqueous solution is washed once with ether (100 ml)
  7. filtrationThe yellow crystalline glyoxalate is filtered off
  8. dry with materialdried over P2O5

출처 및 근거

ORD 기록
ord-3f7e03bc02fb4d5a90f80b73e79af763
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04092325

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