Dimethylformamide → HCID 67338907, compound

HRID 2092345Notes

Reaction equation

HRID 2092345 reaction equation
[C:1]([NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.C1CCCCC1.CN(C)[CH:28]=[O:29]>C1COCC1.O>[C:1]([N:5]1[CH:28]([OH:29])[C:8]2[C:7](=[CH:12][CH:11]=[C:10]([CH3:13])[CH:9]=2)[C:6]1=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8078CyclohexaneHCID 576940N-tert-Butyl-4-methylbenzamideHCID 178418400CID 53628100

Product 1

HCID 67338907HCID 67338907, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-tert-butyl-4-methylbenzamide (9.02 g, 47.2 mmol) in THF (132 ml), charged to a 250 mL round bottom, sec-butyl lithium, 1.4 m in cyclohexane (74.1 ml, 104 mmol) was added at −78° C. The reaction mixture was stirred at −78° C. for 30 min, then warmed to 0° C. for 45 min, before cooling back to −78° C. Then N,N-dimethylformamide (12.0 ml, 156 mmol) was added. The reaction mixture was stirred at −78° C. for 30 min, then allowed to warm to 23° C. The reaction mixture was diluted with water and extracted with EtOAc 3×. The combined organics were washed with brine, dried over magnesium sulfate and concentrated under vacuum to give 2-tert-butyl-3-hydroxy-5-methylisoindolin-1-one (10.6 g, 100% yield). MS (M+H)+ 220.

Workup

  1. temperaturewarmed to 0° C. for 45 min
  2. temperaturebefore cooling back to −78° C
  3. stirringThe reaction mixture was stirred at −78° C. for 30 min
  4. temperatureto warm to 23° C
  5. extractionextracted with EtOAc 3×
  6. washThe combined organics were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8f80ff19f0e94775a510bda618589ede
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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