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

HRID 962767

반응식

HRID 962767 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[OH:27])[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[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[O:27][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 19079832Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate

생성물 1

HCID 19085543Ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy)benzoyl]indol-1-yl}butanoate수율 37.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate (5.70 g) was dissolved in N,N-dimethylformamide (40 ml). α-bromo-p-xylene (3.72 g) and potassium carbonate (2.57 g) were added to the resultant solution and stirred for 3 hours at room temperature. 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 2.77 g of ethyl 4-{3-[3-hydroxy-4-(4-methylphenylmethoxy)benzoyl]indol-1-yl}butanoate (2.77 g) as light brown crystals.

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-b9e886295b7646c8a317bc6ffb7d90fc
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760040

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