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

HRID 619833

반응식

HRID 619833 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.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:8][CH2:7][C:4]1[CH:3]=[C:2]([C:9]#[N:10])[S:6][CH:5]=1

참가 물질

6

반응물 2

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

생성물 1

HCID 106542884-(Hydroxymethyl)thiophene-2-carbonitrile

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of (5-iodothiophene-3-yl)methanol (42 g, 176 mmol) in 150 mL of DMF is added Zn(CN)2 (12.4 g, 106 mmol) and Pd(PPh3)4 (8.13 g, 7.04 mmol). The solution is heated to 80° C. After 6 hours, the solution is diluted with 3 L of EtOAc. The resulting solution is washed with 1 N 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 1 N 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-bd47b668258a41c0903fc816ad49a343
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958918

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