Potassium Carbonate → ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate

HRID 591521Notes

Reaction equation

HRID 591521 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10](=[O:23])[CH2:11][C:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]=O)=[CH:20][C:15]=2[S:14][CH:13]=1)[CH3:8].[Cl-:24].[CH3:25][C:26]1[C:31]([CH2:32][P+:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:30][CH:29]=[C:28]([CH3:52])[N:27]=1>CN(C=O)C>[CH2:7]([O:9][C:10](=[O:23])[CH2:11][C:12]1[C:16]2[CH:17]=[CH:18][C:19](/[CH:21]=[CH:32]/[C:31]3[C:26]([CH3:25])=[N:27][C:28]([CH3:52])=[CH:29][CH:30]=3)=[CH:20][C:15]=2[S:14][CH:13]=1)[CH3:8].[Cl-:24].[CH3:25][C:26]1[C:31]([CH2:32][P+:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:30][CH:29]=[C:28]([CH3:52])[N:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 118656271((2,6-Dimethylpyridin-3-yl)methyl)(triphenyl)phosphonium chlorideHCID 131734528Ethyl(6-formyl-1-benzothiophen-3-yl)acetate

Product 2

HCID 89775432ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetateHCID 118656271((2,6-Dimethylpyridin-3-yl)methyl)(triphenyl)phosphonium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of K2CO3 (134 mg), ethyl(6-formyl-1-benzothiophen-3-yl)acetate (160 mg), ((2,6-dimethylpyridin-3-yl)methyl) (triphenyl)phosphonium chloride (323 mg) and DMF (5 mL) was stirred at room temperature for 3 d. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate (example 179, 60 mg) and ethyl(6-((Z)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate (example 180, 110 mg).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-b32954b935b64ccba76a58ff8a27a0f3
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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