Citric Acid → HCID 178487492, 화합물

HRID 392579노트

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HRID 392579 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 178487492HCID 178487492, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-20e5d771f14d45b690271d4c31551114
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800778B1

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