Triethylamine → 3-Benzylpyrrolylmethyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate

HRID 27942Notes

Reaction equation

HRID 27942 reaction equation
[CH2:1]([C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]2[S:30][C:29]([CH:31]([CH:35]([CH3:37])[CH3:36])[C:32](O)=[O:33])=[CH:28][C:27]=2[CH:38]=1>CCOCC>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]2[S:30][C:29]([CH:31]([CH:35]([CH3:36])[CH3:37])[C:32]([O:14][CH2:13][C:9]3[NH:10][CH:11]=[CH:12][C:8]=3[CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:33])=[CH:28][C:27]=2[CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 542046732-(5-Chloro-2-benzothienyl)-3-methylbutanoic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

Product 1

HCID 538193603-Benzylpyrrolylmethyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 3-benzylpyrrolylmethyl alcohol (0.99 mmol) and triethylamine (0.14 g, 1.38 mmol) in ether (about15 ml), under nitrogen, is added a solution of the acid chloride of 2-(5-chloro-2-benzothienyl)-3-methylbutanoic acid (1.5 mmol) in either. The mixture is stirred for about 60 minutes and then quenched with saturated aqueous NaHCO3. The ether phase is washed with aqueous NaHCO3, water and brine, dried over sodium sulfate and solvent evaporated to give 3-benzylpyrrolylmethyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. washThe ether phase is washed with aqueous NaHCO3, water and brine
  3. dry with materialdried over sodium sulfate and solvent
  4. customevaporated

Sources & evidence

ORD record
ord-e36692f08a234bc38464e8cd379707aa
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

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