Dimethylformamide dimethyl acetal → HCID 71114823, compound

HRID 1624053Notes

Reaction equation

HRID 1624053 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:16])[CH2:4][C:3]1=[O:17].CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[CH3:21][N:22](/[CH:24]=[C:4]1/[CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:16])[CH2:6][CH2:7][C:2]([CH3:18])([CH3:1])[C:3]/1=[O:17])[CH3:23]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 71114867HCID 71114867, compound

Product 1

HCID 71114823HCID 71114823, compoundYield 27%

Procedure

4-(4,4-Dimethyl-3-oxo-cyclohexyl)-3-methyl-benzonitrile (0.6 g, 2.49 mmol) in N,N-dimethylformamide dimethylacetal (50 mL) is stirred at 90° C. for two days. The mixture is cooled to room temperature and concentrated in vacuo. The residue is diluted with ethyl acetate (50 mL) and water (50 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (3×50 mL). The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel flash chromatography, eluting with pet ether:EtOAc 1:1 to MeOH:DCM=1:30 to give 4-[(2Z)-2-(dimethylaminomethylene)-4,4-dimethyl-3-oxo-cyclohexyl]-3-methyl-benzonitrile (0.2 g, 27%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is diluted with ethyl acetate (50 mL) and water (50 mL)
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with ethyl acetate (3×50 mL)
  5. washThe combined organic phase is washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel flash chromatography
  9. washeluting with pet ether:EtOAc 1:1 to MeOH

Sources & evidence

ORD record
ord-3555c86ad52c47f3971de1e06ea9aa19
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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