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

HRID 27946Notes

Reaction equation

HRID 27946 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c40e7b1588574efd95d601e70ef488b0
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

Loading…