Dimethylformamide → HCID 23448413、化合物

HRID 1838786ノート

反応式

HRID 1838786 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:15]([OH:17])=[O:16].[N:18]12CCCN=C1C[CH2:22][CH2:21][CH2:20][CH2:19]2.BrCCCC#N.CN(C)C=O>O>[C:19]([CH2:20][CH2:21][CH2:22][O:16][C:15]([C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[CH:6]=[CH:7][C:2]=1[OH:1])=[O:17])#[N:18]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 214124-BromobutyronitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 234484124,4'-Dihydroxy-3-biphenylcarboxylic acid

生成物 1

HCID 23448413HCID 23448413、化合物収率 70.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

A mixture of 4,4′-dihydroxy-3-biphenylcarboxylic acid (2.3 g; 10 mmol), 1,8-diaza-bicyclo[5.4.0]undec-7-ene (1.7 g; 11.2 mmol), 4-bromobutyronitrile (1.7 g; 11.2 mmol) and N,N-dimethylformamide (40 ml) was heated at 75° C. for 4 h. The reaction mixture was cooled, poured into water (300 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and with water (2×100 ml), dried over magnesium sulphate and filtered. The organic solvent was removed in vacuo. The residue (3.0 g) was purified by flash chromatography using a silica gel column and toluene/ethyl acetate (97:3) as eluent to give 2.1 g (70%) of 3-cyanopropyl-4,4′-dihydroxy-3-biphenylcarboxylate.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and with water (2×100 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customThe organic solvent was removed in vacuo
  7. customThe residue (3.0 g) was purified by flash chromatography

出典と根拠

ORDレコード
ord-2886ad5849364beb97265f158bb7008f
出典データセット
uspto-grants-2004_01
特許番号
US06676851B1

反応ノート

読み込み中…