Dimethylformamide → 4-(Hydroxymethyl)thiophene-2-carbonitrile

HRID 2748

반응식

HRID 2748 반응식
I[C:2]1[S:6][CH:5]=[C:4]([CH2:7][OH:8])[CH:3]=1.[CH3:9][N:10](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[OH:8][CH2:7][C:4]1[CH:3]=[C:2]([C:9]#[N:10])[S:6][CH:5]=1

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 22559990(5-Iodothiophen-3-yl)methanol

생성물 1

HCID 106542884-(Hydroxymethyl)thiophene-2-carbonitrile

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of (5-iodo-thiophene-3-yl)methanol (42 g, 176 mmol) in 150 mL of DMF is added zinc cyanide (12.4 g, 106 mmol) and tetrakis(triphenylphospine)palladium (0) (8.13 g, 7.04 mmol). The solution is heated to 80° C. After 6 h, the solution is diluted with 3 L of EtOAc. The resulting solution is washed with 1N NH4OH, H2O and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (10 g, 72 mmol) as a clear oil.

후처리

  1. washThe resulting solution is washed with 1N NH4OH, H2O and sat. NaCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-e6dea7c2aa4947e5bcc870d26f4d2244
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731315

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