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Potassium Carbonate → 6-[2-(1H-Imidazole-4-yl)-ethoxy]-2-(1-phenyl-ethylidene)-3,4-dihydro-2H-naphthalen-1-one

HRID 368331
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HRID 368331 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7](=[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].Br.Br[CH2:29][CH2:30][C:31]1[N:32]=[CH:33][NH:34][CH:35]=1>CN(C=O)C.O>[NH:34]1[CH:35]=[C:31]([CH2:30][CH2:29][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[C:7](=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:6][CH2:5]3)[N:32]=[CH:33]1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 539278676-Hydroxy-2-(1-phenyl-ethylidene)-3,4-dihydro-2H-naphthalen-1-oneHCID 178419249HCID 178419249, 화합물

생성물 1

HCID 1784355456-[2-(1H-Imidazole-4-yl)-ethoxy]-2-(1-phenyl-ethylidene)-3,4-dihydro-2H-naphthalen-1-one수율 49.2%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

실험 절차

The product obtained from Step 2 (0.180 g, 0.68 mmol) was dissolved in 5 mL of dry DMF and treated with K2CO3 (0.376 g, 2.72 mmol) and 4-(2-bromoethyl)imidazole hydrobromide (0.192 g, 0.75 mmol). After stirring overnight at room temperature, the reaction was diluted with water and extracted with EtOAc. The pooled extracts were washed well with aqueous 0.5N KOH, water and brine, and then dried, filtered, and concentrated. Purification of the residue (SiO2, 5% MeOH in DCM) afforded 0.120 g (49%) of the title compound as a light yellow foam. Conversion of this product to its HCl salt according to the method of Example 34 afforded 0.063 g of a light yellow powder, mp 170-172° C.: CI-MS m/e 359 (M+ +1).

후처리

  1. extractionextracted with EtOAc
  2. washThe pooled extracts were washed well with aqueous 0.5N KOH, water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue (SiO2, 5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-e19a4046fc01401eb37cf121dec1ba59
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06133303

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