Ethyl Acrylate → HCID 67168262, compound
Reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:31]1[S:40][C:39]2[C:38](=[O:41])[C:37]3[CH:42]=[CH:43][CH:44]=[CH:45][C:36]=3[CH2:35][CH2:34][C:33]=2[CH:32]=1.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C.C(N(CC)CC)C>[O:41]=[C:38]1[C:37]2[CH:42]=[CH:43][CH:44]=[CH:45][C:36]=2[CH2:35][CH2:34][C:33]2[CH:32]=[C:31]([CH:3]=[CH:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[S:40][C:39]1=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Triethylamine (34 mL), ethyl acrylate (27.5 mL), palladium acetate (0.4 g), and P(o-Tol)3 (1.5 g) were added to a DMF (50 mL) solution of 2-bromo-9,10-dihydro-3-thiabenzo[f]azulen-4-one (7.00 g), and the mixture was stirred overnight at 80° C. in an argon atmosphere. An aqueous saturated ammonium chloride solution was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the organic layer was then washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure, and the residue obtained was purified by silica gel column chromatography (chloroform-methanol=9:1), to give 6.39 g (85%) of the captioned compound as an amorphous solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washthe organic layer was then washed with an aqueous saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under a reduced pressure
- customthe residue obtained
- customwas purified by silica gel column chromatography (chloroform-methanol=9:1)
Sources & evidence
- ORD record
- ord-3eadc6323f1d4a7988a4ba80c47d7483
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653285B2
Reaction notes
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