Dimethylformamide → HCID 23295004, compound

HRID 1955282Notes

Reaction equation

HRID 1955282 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#N)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(C)C=CC(S(O[CH2:22][C:23]([CH3:29])([CH3:28])[CH2:24][CH2:25][CH2:26]O)(=O)=O)=CC=1.C[N:32]([CH:34]=O)C>CCCCCC>[C:3]1([C:9]2([CH2:10][C:34]#[N:32])[CH2:26][CH2:25][CH2:24][C:23]([CH3:29])([CH3:28])[CH2:22]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 86755866HCID 86755866, compound

Product 1

HCID 23295004HCID 23295004, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

NaH (60% dispersion in mineral oil, 72.3 mmol) was washed several times with n-hexane and suspended in DMF. A mixture of phenylacetonitrile (24.1 mmol) and de-O-p-toluene-sulfonyl-2,2-dimethyl-1,5-pentanediol (24.1 mmol) in DMF was added dropwise. The reaction mixture was stirred at 70° C. for 3 h and DMF was evaporated under reduced pressure. Excess hydride was then decomposed by the cautious addition of H2O. Extraction with Et2O, drying of the organic layer (MgSO4) and evaporation of the solvent afforded 1-phenyl-3,3-dimethylcyclohexaneacetonitrile that was chromatographed on silica using petroleumether-EtOAc 98:2 as eluent; 1H NMR (CDCl3) δ 0.96 (s, 3H), 1.26 (m, 1H), 1.31 (m, 3H) 1.59 (m, 2H), 1.78 (m, 2H), 1.92 (m, 2H), 2.23 (m, 1H), 7.49 (m, 5H). 7.0 mmol of the nitrile was refluxed with KOH (40%, 15 mL) in ethyleneglycol (40 mL) for two days. It was then allowed to cool to room temperature and was extracted with Et2O. The aqueous layer was acidified and extracted with Et2O. The organic layer was dried (MgSO4) and concentrated to provide 1.5 g (27%) of the desired carboxylic acid.

Workup

  1. additionwas added dropwise
  2. customDMF was evaporated under reduced pressure
  3. additionExcess hydride was then decomposed by the cautious addition of H2O
  4. extractionExtraction with Et2O
  5. dry with materialdrying of the organic layer (MgSO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-462332fc85fb4e76a1e6f43f7899cd0f
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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