Dimethylformamide dimethyl acetal → HCID 71114823, 화합물

HRID 1624053노트

반응식

HRID 1624053 반응식
[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]

참가 물질

3

반응물 2

HCID 78373Dimethylformamide dimethyl acetalHCID 71114867HCID 71114867, 화합물

생성물 1

HCID 71114823HCID 71114823, 화합물수율 27%

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-3555c86ad52c47f3971de1e06ea9aa19
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778984B2

반응 노트

불러오는 중…