2-Methyl-2-phenylpropanal → (S)-N-(2-Methyl-2-phenylpropylidene)-p-toluenesulfinamide

HRID 966432

Reaction equation

HRID 966432 reaction equation
CC1(C)C(C2C=CC=CC=2)O1.[CH3:12][C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH:14]=O.[C:23]1([CH3:32])[CH:28]=[CH:27][C:26]([S@@:29]([NH2:31])=[O:30])=[CH:25][CH:24]=1>C1C=CC=CC=1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.FC1C(B(C2C(F)=C(F)C(F)=C(F)C=2F)C2C(F)=C(F)C(F)=C(F)C=2F)=C(F)C(F)=C(F)C=1F>[CH3:12][C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH:14]=[N:31][S@:29]([C:26]1[CH:27]=[CH:28][C:23]([CH3:32])=[CH:24][CH:25]=1)=[O:30]

Participants

7

Reactant 3

HCID 2838792-Methyl-2-phenylpropanalHCID 57433552,2-Dimethyl-3-phenyloxiraneHCID 11116285(S)-4-methylbenzenesulfinamide

Product 1

HCID 69625671(S)-N-(2-Methyl-2-phenylpropylidene)-p-toluenesulfinamideYield 81%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 241BenzeneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2.5 g of 2,2-dimethyl-3-phenyloxirane (16 mmol) in 85 mL of anhydrous benzene is added 0.415 g (0.362 mmol, 5 mol %) of tris(pentafluorophenyl) borane. The light yellow solution is stirred at 25° C. for 19 hours. The reaction mixture containing the 2-methyl-2-phenylpropanal is then treated with (S)-p-toluenesulfinamide (2.3 g, 15 mmol) followed by a solution of 16 mL (73 mmol) titanium ethoxide in 155 mL of benzene. The yellow solution is stirred at 25° C. for 24 hours then cooled to 5-10° C. and quenched with 245 mL of water. The mixture is filtered through diatomaceous earth, and the filter cake washed with methylene chloride (4×50 mL). The aqueous layer is washed with methylene chloride (1×25 mL). The combined organic layers are dried (MgSO4) and concentrated under reduced pressure to give 3.74 g (81%) of the desired product as a white solid. The product is used without further purification in the next step.

Workup

  1. stirringThe yellow solution is stirred at 25° C. for 24 hours
  2. temperaturethen cooled to 5-10° C.
  3. customquenched with 245 mL of water
  4. filtrationThe mixture is filtered through diatomaceous earth
  5. washthe filter cake washed with methylene chloride (4×50 mL)
  6. washThe aqueous layer is washed with methylene chloride (1×25 mL)
  7. dry with materialThe combined organic layers are dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a21d45c9fa064fad827402ad2f202479
Source dataset
uspto-grants-2005_10
Patent number
US06951955B2

Linked notes

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