tert-Butyl methyl ether → HCID 68486961, compound

HRID 1882336Notes

Reaction equation

HRID 1882336 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]=[C:21]([O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:22]=[CH:23]S(C3C=CC=CC=3)(=O)=O)=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.COC(C)(C)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:23]=[CH:22][C:21](=[N:20][C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[CH2:11][CH2:12][CH2:13]3)[O:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 68491489HCID 68491489, compound

Product 1

HCID 68486961HCID 68486961, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-fluorothiophenol (0.22 g) in DMF (6 mL) was added 60% sodium hydride (84 mg), and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. The reaction mixture was added to a solution of phenyl N-(5-indanyl)-3-(phenylsulfonyl)acrylimidate (0.65 g) in anhydrous DMF (3 mL) under ice-cooling. The mixture was stirred at room temperature for 2 hours. To the reaction mixture was added tert-butyl methyl ether (50 mL), which was washed with a 1N aqueous sodium hydroxide solution, water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was isolated and purified by medium pressure preparative liquid chromatography (Yamazen SI-40B, hexane:ethyl acetate=19:1) to obtain phenyl 3-(4-fluorophenylthio)-N-(5-indanyl)acrylimidate (0.16 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. washwas washed with a 1N aqueous sodium hydroxide solution, water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was isolated
  7. custompurified by medium pressure preparative liquid chromatography (Yamazen SI-40B, hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-25a01bd9298c4e67b0f3a03113064abe
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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