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

HRID 27946ノート

反応式

HRID 27946 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c40e7b1588574efd95d601e70ef488b0
出典データセット
uspto-grants-1980_09
特許番号
US04224330

反応ノート

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