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

HRID 619833

反応式

HRID 619833 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 106542884-(Hydroxymethyl)thiophene-2-carbonitrile

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bd47b668258a41c0903fc816ad49a343
出典データセット
uspto-grants-1999_09
特許番号
US05958918

関連ノート

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