Sodium amide → Methyl 3-[4-[1-[2-[3-isopropyl-6-(trifluoromethyl)-benzothiophen-2-yl]ethyl]vinyl]-2-methylphenyl]propionate

HRID 241377Notes

Reaction equation

HRID 241377 reaction equation
[Br-].[CH3:2][PH+](C)C.[NH2-].[Na+].[CH:8]([C:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:14]=2[S:13][C:12]=1[CH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:30]([CH3:40])[CH:29]=1)=O)([CH3:10])[CH3:9].[Cl-].[NH4+]>C1COCC1>[CH:8]([C:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]([F:22])([F:23])[F:21])=[CH:19][C:14]=2[S:13][C:12]=1[CH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:30]([CH3:40])[CH:29]=1)=[CH2:2])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 24533Sodium amideHCID 25517Ammonium ChlorideHCID 22062633Trimethylphosphonium bromideHCID 66883002Methyl 3-[4-[3-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]propionyl]-2-methylphenyl]propionate

Product 1

HCID 66884459Methyl 3-[4-[1-[2-[3-isopropyl-6-(trifluoromethyl)-benzothiophen-2-yl]ethyl]vinyl]-2-methylphenyl]propionateYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of trimethylphosphonium bromide (84 mg, 0.24 mmol) in THF (4 mL) was added sodium amide (12 mg, 0.31 mmol) under N2 atmosphere. The mixture was stirred for 30 minutes at room temperature, to which was added a solution of methyl 3-[4-[3-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]propionyl]-2-methylphenyl]propionate [Example 12 (7)] (75 mg, 0.16 mmol) in THF (1 mL). The mixture was stirred for 22 hours at room temperature, treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1), to give the titled compound as a pale yellow oil (27 mg, yield 36%).

Workup

  1. stirringThe mixture was stirred for 22 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-206b1abdfa8c40adbd096a311bc4b394
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

Loading…