Water → 3-Benzylpyrrolylmethyl 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoate

HRID 27946노트

반응식

HRID 27946 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])=[CH:8][C:7]=2[CH:18]=1.S(Cl)(Cl)=O.[CH2:25]([C:32]1[CH:36]=[CH:35][NH:34][C:33]=1[CH2:37]O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C.C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:20][C:2]([F:19])([F:1])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([O:14][CH2:37][C:33]3[NH:34][CH:35]=[CH:36][C:32]=3[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:13])=[CH:8][C:7]=2[CH:18]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 539457852-(5-Trifluoromethyl-2-benzothienyl)-3-methylbutanoic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

생성물 1

HCID 542765353-Benzylpyrrolylmethyl 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoate

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 241Benzene용매

실험 절차

A mixture of 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoic acid (3.95 mmol), thionyl chloride (0.342 ml, 4.74 mmol) and DMF (several drops) in 50 ml benzene is stirred at RT for 2 days. The solvent and excess thionyl chloride are evaporated under reduced pressure. The resulting acid chloride is dissolved in 50 ml benzene, and 3-benzylpyrrolylmethyl alcohol (3.95 mmol) and 0.482 g 4-dimethylaminopyridine (3.95 mmol) are added. The mixture is left at 25° for 18 hours and then heated under reflux for 2 hours. The mixture is then poured into water and extracted with ether. The organic phase is washed with dilute HCL, sat. NaHCO3, water and brine, dried and solvent removed under vacuum to yield 3-benzylpyrrolylmethyl 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoate.

후처리

  1. customThe solvent and excess thionyl chloride are evaporated under reduced pressure
  2. dissolutionThe resulting acid chloride is dissolved in 50 ml benzene
  3. waitThe mixture is left at 25° for 18 hours
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. extractionextracted with ether
  7. washThe organic phase is washed with dilute HCL, sat. NaHCO3, water and brine
  8. customdried
  9. customsolvent removed under vacuum

출처 및 근거

ORD 기록
ord-c40e7b1588574efd95d601e70ef488b0
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04224330

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