Hydrochloric Acid → Ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate

HRID 962768

반응식

HRID 962768 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6].Br[CH2:37][CH2:38][CH2:39][Cl:40].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][O:27][C:26]2[CH:25]=[CH:24][C:4]([C:5]([C:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=3)=[O:6])=[CH:3][C:2]=2[O:1][CH2:37][CH2:38][CH2:39][Cl:40])=[CH:30][CH:31]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 19085543Ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy)benzoyl]indol-1-yl}butanoate

생성물 1

HCID 19085526Ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate수율 82.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

Ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy) benzoyl]indol-1-yl}butanoate (2.77 g) obtained in Step 1 was dissolved in N,N-dimethylformamide (30 ml). 1-Bromo-3-chloropropane (1.39 g) and potassium carbonate (0.97 g) were added to the resultant solution and stirred for 6 hours at 60° C. The reaction mixture was poured into 2N HCl and extracted with ethyl acetate. The resultant extract was sequentially washed with saturated sodium bicarbonate solution and brine and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), obtaining 2.67 g of ethyl 4-{3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate as a light yellow oily substance.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe resultant extract
  3. washwas sequentially washed with saturated sodium bicarbonate solution and brine
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-c49e09dbb9cf4c169bcb362f5e6dd098
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760040

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