Citric Acid → HCID 178487492、化合物

HRID 392579ノート

反応式

HRID 392579 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[CH2:14]([Li])[CH2:15][CH2:16]C.[CH:19]([C:21]1[N:22]=[CH:23][N:24](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:25]=1)=[O:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCCCCC>[NH:24]1[CH:25]=[C:21]([C:19]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[CH:3]=2)([OH:20])[CH:15]([CH3:16])[CH3:14])[N:22]=[CH:23]1

参加物

7

反応物 4

HCID 311Citric AcidHCID 787862-Bromo-6-methoxynaphthaleneHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418339Butyllithium

生成物 1

HCID 178487492HCID 178487492、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

2-Bromo-6-methoxynaphthalene (30 g) was dissolved in THF (400 ml) and cooled to −78° C. A solution (1.6 M; 99 ml) of n-butyl lithium in hexane was added dropwise, and the mixture was stirred at −78° C. for 30 min. A solution (300 ml) of 4-formyl-1-trityl-1H-imidazol (38.9 g) in THF was slowly added dropwise. After stirring at −78° C. for 30 min, the reaction mixture was poured into 3% aqueous citric acid solution (600 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layer was combined and the mixture was washed with saturated brine, dried and concentrated. The residue was washed with ethyl acetate to give the title compound (35.0 g) as a colorless solid.

後処理

  1. stirringAfter stirring at −78° C. for 30 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe mixture was washed with saturated brine
  5. customdried
  6. concentrationconcentrated
  7. washThe residue was washed with ethyl acetate

出典と根拠

ORDレコード
ord-20e5d771f14d45b690271d4c31551114
出典データセット
uspto-grants-2004_10
特許番号
US06800778B1

反応ノート

読み込み中…