Hydrochloric Acid → HCID 66883212, compound

HRID 241364Notes

Reaction equation

HRID 241364 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH2:15])C(OC)=O)=[C:6]([CH3:16])[CH:5]=1)(=[O:3])[CH3:2].[CH3:17][O:18][Na].[CH3:20][OH:21].[CH3:22][C:23]1[C:27]2[CH:28]=[CH:29][C:30]([C:32]([F:35])([F:34])[F:33])=[CH:31][C:26]=2[S:25][C:24]=1[CH:36]=O.Cl>C1COCC1>[CH3:22][C:23]1[C:27]2[CH:28]=[CH:29][C:30]([C:32]([F:33])([F:34])[F:35])=[CH:31][C:26]=2[S:25][C:24]=1[CH:36]=[CH:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:15][C:20]([O:18][CH3:17])=[O:21])=[C:6]([CH3:16])[CH:5]=1)=[O:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86652862HCID 86652862, compoundHCID 86652863HCID 86652863, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 66883212HCID 66883212, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold suspension of methyl (4-acetyl-2-methylphenyl)acrylate [WO 2007119887] (89 mg, 0.41 mmol) and powdered Molecular sieves 3A (250 mg) in THF (2 mL) was added 0.5M MeONa in MeOH (1.0 mL, 0.49 mmol) under N2 atmosphere. The mixture was stirred for 10 minutes under ice-cooling, to which was added slowly a solution of 3-methyl-6-(trifluoromethyl)benzothiophen-2-carboxaldehyde (100 mg, 0.410 mmol) in THF (1.7 mL). The mixture was stirred for 4 hours under ice-cooling, neutralized with 1N hydrochloric acid, and filtered. The filtrate was washed with water, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the titled compound as a yellow crystal (87 mg, 48%).

Workup

  1. temperaturecooling, to which
  2. stirringThe mixture was stirred for 4 hours under ice-
  3. filtrationfiltered
  4. washThe filtrate was washed with water
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d93ae83ce97b4cb2a9b07925de73829d
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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