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}-acrylic acid

HRID 1013444Notes

Reaction equation

HRID 1013444 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[CH:28]=[CH:29][C:30]([OH:32])=[O:31])[CH3:18].Cl>[OH-].[Na+]>[CH2:17]([C:19]1[CH:24]=[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:22]=[C:21]([CH3:27])[C:20]=1[CH:28]=[CH:29][C:30]([OH:32])=[O:31])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 574374251-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanoneHCID 765393093-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acid

Product 1

HCID 673171353-{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}-acrylic acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (200 mg, 0.846 mmol) and 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid (203 mg, 0.931 mmol) in methanolic NaOH (8 mL, 10 g NaOH in 100 mL methanol) is stirred at rt for 3 h before it is carefully acidified to pH 1 by adding 2 N aq. HCl. The mixture is extracted twice with DCM and the organic extracts are washed with water and brine, dried over MgSO4, filtered and evaporated. The crude product is crystallised from acetonitrile (40 mL) 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}-acrylic acid (222 mg) as yellow crystals. From the mother liquor a second crop (29 mg) of product can be obtained after purification by prep. HPLC (Grom-Sil 120 ODS-4-HE, 30×75 mm, 10 μm, acetonitrile/water (0.5% HCOOH), 20% to 95% acetonitrile); LC-MS: tR=1.20 min, [M+1]=437.31.

Workup

  1. extractionThe mixture is extracted twice with DCM
  2. washthe organic extracts are washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is crystallised from acetonitrile (40 mL)

Sources & evidence

ORD record
ord-79d980b6a8d84f6992c80ce8c43213c6
Source dataset
uspto-grants-2011_07
Patent number
US07981924B2

Reaction notes

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