4-Hydroxybenzaldehyde → 4-(4-(2-Quinolinylmethyloxy)styryl)phenol

HRID 2073869ノート

反応式

HRID 2073869 の反応式
[Cl-].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][O:13][C:14]1[CH:39]=[CH:38][C:17]([CH2:18][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:16][CH:15]=1.[H-].[Na+].[OH:42][C:43]1[CH:50]=[CH:49][C:46]([CH:47]=O)=[CH:45][CH:44]=1>CN(C=O)C>[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[CH:47][C:46]2[CH:49]=[CH:50][C:43]([OH:42])=[CH:44][CH:45]=2)=[CH:38][CH:39]=1

参加物

5

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 198089424-(2-Quinolinylmethyloxy)benzyl triphenylphosphonium chloride

生成物 1

HCID 539691924-(4-(2-Quinolinylmethyloxy)styryl)phenol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of (13.29 mmol) of 4-(2-quinolinylmethyloxy)benzyl triphenylphosphonium chloride in 100 ml of dry DMF under positive nitrogen atmosphere is cooled to 0° C. and 0.50 g (20.77 mmol), of an 80% NaH in oil dispersion is added in small portions. The suspension is aged for 15 minutes at 0° C. followed by 45 minutes at room temperature to assure complete anion formation. The flask is cooled back to 0° C. and (13.29 mmol) of 4-hydroxybenzaldehyde in 20 ml of DMF is dropped in over a period of 15 minutes. The reaction is allowed to equilibrate to room temperature and stirred for 2 hours. The resultant mixture is poured into ice water and filtered. The precipitate is dissolved in CH2Cl2, dried, and concentrated in vacuo. The crude product is recrystallized from ether to give 4-(4-(2-quinolinylmethyloxy)styryl)phenol.

後処理

  1. waitfollowed by 45 minutes at room temperature
  2. temperatureThe flask is cooled back to 0° C.
  3. customto equilibrate to room temperature
  4. filtrationfiltered
  5. dissolutionThe precipitate is dissolved in CH2Cl2
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe crude product is recrystallized from ether

出典と根拠

ORDレコード
ord-2fd738126b42402d808f97fd87fd276c
出典データセット
uspto-grants-1990_04
特許番号
US04920130

反応ノート

読み込み中…