Benzyl Alcohol → HCID 68488200, compound

HRID 1882337Notes

Reaction equation

HRID 1882337 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][C:12]1[CH:13]=[C:14]([N:19]=[C:20]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[CH:21]=[CH:22]S(C2C=CC=CC=2)(=O)=O)[CH:15]=[CH:16][C:17]=1[CH3:18].COC(C)(C)C>C1COCC1>[CH2:1]([O:8][CH:22]=[CH:21][C:20](=[N:19][C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([CH3:11])[CH:13]=1)[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 68488053HCID 68488053, compound

Product 1

HCID 68488200HCID 68488200, compoundYield 114.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl alcohol (0.78 g) in THF (15 mL) was added 60% sodium hydride (90 mg) under a nitrogen atmosphere under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was added dropwise to a solution of 3-methylphenyl N-(3,4-dimethylphenyl)-3-(phenylsulfonyl)acrylimidate (0.78 g) in anhydrous THF (15 mL) under ice-cooling. The mixture was stirred at the same temperature for 3 hours. To the reaction mixture was added tert-butyl methyl ether (80 mL), which was washed with a 1N aqueous sodium hydroxide solution, water and then a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 3-methylphenyl 3-benzyloxy-N-(3,4-dimethylphenyl)acrylimidate (0.82 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture was stirred at the same temperature for 3 hours
  4. washwas washed with a 1N aqueous sodium hydroxide solution, water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e4a79fceedf8493f841bda584c49e200
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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