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

HRID 1665957Notes

Reaction equation

HRID 1665957 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:17][CH2:16][C:5]2=[C:6]([C:13](=[O:15])[CH3:14])[S:7][C:8]([C:9]([F:12])([F:11])[F:10])=[C:4]2[CH2:3]1.[CH2:19]([C:21]1[CH:26]=[C:25]([CH:27]=O)[CH:24]=[C:23]([CH3:29])[C:22]=1[CH:30]=[CH:31][C:32]([OH:34])=[O:33])[CH3:20].Cl.[CH2:36](O)[CH3:37]>C(O)(C)C.C([O-])(O)=O.[Na+]>[CH2:36]([O:34][C:32](=[O:33])[CH:31]=[CH:30][C:22]1[C:23]([CH3:29])=[CH:24][C:25]([CH:27]=[CH:14][C:13]([C:6]2[S:7][C:8]([C:9]([F:12])([F:10])[F:11])=[C:4]3[CH2:3][C:2]([CH3:18])([CH3:1])[CH2:17][CH2:16][C:5]=23)=[O:15])=[CH:26][C:21]=1[CH2:19][CH3:20])[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 575089061-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanoneHCID 765393093-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acid

Product 1

HCID 671883473-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (500 mg, 1.81 mmol) and 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid (395 mg, 1.81 mmol) in ethanol (25 mL) is treated with 5 N HCl in isopropanol (15 mL). The orange brown reaction mixture is stirred at 65° C. for 64 h. The mixture is diluted with sat. aq. NaHCO3 solution and extracted twice with EA. The organic extracts are washed with sat. NaHCO3 solution, dried over MgSO4, filtered and the solvent of the filtrate is evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester (634 mg, contains traces of the corresponding isopropyl ester) as a colourless oil; LC-MS: tR=1.32 min, [M+1]=505.04.

Workup

  1. extractionextracted twice with EA
  2. washThe organic extracts are washed with sat. NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent of the filtrate is evaporated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-7fc677ff6c9247cab480c0dfed2b6fc3
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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