Hydrochloric Acid → 3-{2-Ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-6-methyl-phenyl}-propionic acid ethyl ester

HRID 1013443Notes

Reaction equation

HRID 1013443 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)[CH3:2].[CH2:17]([C:19]1[CH:24]=[C:23]([CH:25]=O)[CH:22]=[C:21]([CH3:27])[C:20]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH3:18].Cl.[CH3:34][CH2:35]N(C(C)C)C(C)C>C(O)C.C(O)(C)C>[CH2:34]([O:32][C:30](=[O:31])[CH2:29][CH2:28][C:20]1[C:21]([CH3:27])=[CH:22][C:23]([CH:25]=[CH:9][C:8]([C:6]2[S:7][C:3]([CH2:1][CH3:2])=[C:4]3[CH2:14][C:13]([CH3:15])([CH3:16])[CH2:12][CH2:11][C:5]=23)=[O:10])=[CH:24][C:19]=1[CH2:17][CH3:18])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 574374063-(2-Ethyl-4-formyl-6-methylphenyl)propionic acidHCID 574374251-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

Product 1

HCID 673160223-{2-Ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-6-methyl-phenyl}-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (143 mg, 0.606 mmol) and 3-(2-ethyl-4-formyl-6-methyl-phenyl)-propionic acid (200 mg, 0.908 mmol) in ethanol (15 mL) is treated with 5 N HCl in isopropanol (3 mL). The dark brown reaction mixture is stirred at rt for 3 h, then at 50° C. for 48 h before DIPEA (4 mL) is added. The solvent is removed in vacuo and the crude product is purified by prep. HPLC (Grom-Sil 120 ODS-4-HE, 30×75 mm, 10 μm, acetonitrile/water (0.5% HCOOH), 10% to 95% acetonitrile) to give 3-{2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-6-methyl-phenyl}-propionic acid ethyl ester (157 mg) as a yellow oil; LC-MS: tR=1.27 min, [M+1]=467.43.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude product is purified by prep

Sources & evidence

ORD record
ord-45dc42b3f14b4aefb51a4afb1b85e263
Source dataset
uspto-grants-2011_07
Patent number
US07981924B2

Reaction notes

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