Benzyl Bromide → Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

HRID 913172노트

반응식

HRID 913172 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:22])=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([O:22][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:10]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58012479Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate

생성물 1

HCID 58012512Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate수율 98%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Benzyl bromide (1.32 ml, 11.1 mmol) was added to a stirred solution of diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate (2.45 g, 7.38 mmol) and potassium carbonate (1.53 g, 11.1 mmol) in acetone (50 ml). The reaction mixture was refluxed for 1 hour under an atmosphere of argon. The resulting mixture was evaporated and the residue was partitioned between 2× ethylacetate and brine. The combined organics were washed with water and dried over magnesium sulphate. The clear oil was purified by chromatography on silica gel, eluting with ethyl acetate (0-40%) in hexane to give the title compound as clear oil (3.05 g, 7.23 mmol). LC/MS: Rt=3.77, [MH]+ 423

후처리

  1. temperatureThe reaction mixture was refluxed for 1 hour under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe residue was partitioned between 2× ethylacetate and brine
  4. washThe combined organics were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe clear oil was purified by chromatography on silica gel
  7. washeluting with ethyl acetate (0-40%) in hexane

출처 및 근거

ORD 기록
ord-544897942775406e889de547b19c579b
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026270B2

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