3-Methoxyphenylhydrazine hydrochloride → Methyl 3-[6-methoxy-3-(t-butylthio) indol-2-yl]-2,2-dimethylpropanoate

HRID 327235

반응식

HRID 327235 반응식
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:10]N)[CH:7]=[CH:8][CH:9]=1.[C:12]([S:16][CH2:17][C:18](=O)[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])([CH3:15])([CH3:14])[CH3:13]>C(O)(C)(C)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:7]([C:17]([S:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:18]([CH2:19][C:20]([CH3:25])([CH3:26])[C:21]([O:23][CH3:24])=[O:22])[NH:10]2)=[CH:8][CH:9]=1

참가 물질

4

반응물 2

HCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate

생성물 1

HCID 53636575Methyl 3-[6-methoxy-3-(t-butylthio) indol-2-yl]-2,2-dimethylpropanoate

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

A mixture of 4.2 g of 3-methoxyphenylhydrazine hydrochloride and 4.9 g of methyl 5-(t-butylthio)-2,2-dimethyl-4-oxopentanoate in 100 mL of t-butanol was refluxed for 18 hours. The mixture was cooled to R.T., and evaporated to dryness. The residue was suspended in ether (150 ml) and stirred for 30 min. The salts were filtered and the filtrate evaporated to dryness to give a residue which was chromatographed on flash silica gel using as eluant ethyl acetate:toluene (1:99) to isolate the title compound as the most polar product; m.p. 133° C.

후처리

  1. temperaturewas refluxed for 18 hours
  2. customevaporated to dryness
  3. filtrationThe salts were filtered
  4. customthe filtrate evaporated to dryness
  5. customto give a residue which
  6. customwas chromatographed on flash silica gel using as eluant ethyl acetate:toluene (1:99)

출처 및 근거

ORD 기록
ord-e997d33143774de09203f9999fd673d1
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272145

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