2-Butenoic acid, 4,4-dimethoxy-, methyl ester, (Z)- → Methyl 4-p-tolylsulfonyl-4-methyl-3-dimethoxymethylpentanoate

HRID 236056

반응식

HRID 236056 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]([O:28][CH3:29])[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[O:25].P(O)(O)([O-])=O.[Na+]>C1CCCCC1.O1CCCC1>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([S:9]([C:6]([CH3:7])([CH3:8])[CH:22]([CH:21]([O:28][CH3:29])[O:20][CH3:19])[CH2:23][C:24]([O:26][CH3:27])=[O:25])(=[O:11])=[O:10])=[CH:13][CH:14]=1

참가 물질

7

반응물 4

HCID 5822072-Butenoic acid, 4,4-dimethoxy-, methyl ester, (Z)-HCID 8167921-(Isopropylsulfonyl)-4-methylbenzeneHCID 23672064Monosodium phosphateHCID 178418339Butyllithium

생성물 1

HCID 12850320Methyl 4-p-tolylsulfonyl-4-methyl-3-dimethoxymethylpentanoate수율 49.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

반응 조건

온도
-70 °C

실험 절차

3.4 ml of a 1.95M butyllithium in cyclohexane solution were slowly added at -70° C. to a solution of 1.24 g of p-tolyl isopropyl sulfone in 13 ml of tetrahydrofuran and the mixture was stirred at -70° C. for 15 minutes. Then, a solution of 1 g of methyl 4,4-dimethoxy-2-butenoate in 20 ml of tetrahydrofuran was slowly added to the mixture which was stirred at -70° C. for one hour and poured into a aqueous monosodium phosphate solution. The mixture was extracted with methylene chloride and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 1--1 ether-petroleum ether (b.p.=40°-70° C.) mixture to obtain 1.1 g of methyl 4-p-toluenesulfonyl-4-methyl-3-dimethoxymethyl-pentanoate melting at 110° C.

후처리

  1. stirringwas stirred at -70° C. for one hour
  2. extractionThe mixture was extracted with methylene chloride
  3. customthe organic phase was dried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with a 1--1 ether-petroleum ether (b.p.=40°-70° C.) mixture

출처 및 근거

ORD 기록
ord-47f976d2918344008a7a71679f3e0649
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04642372

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