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

HRID 222422노트

반응식

HRID 222422 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:2]1([CH2:1][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([O:20][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

생성물 1

HCID 58012491Diethyl 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate수율 109.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Benzylbromide (2.95 ml, 24.7 mmol) was added to a stirred solution of diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate (3 g, 9.87 mmol) and potassium carbonate (3.40 g, 24.7 mmol) in acetone (100 ml). The reaction mixture was refluxed for 18 hours under an atmosphere of argon. The resulting mixture was evaporated and the reaction mixture triturated with water. The resulting tan coloured solid was collected by filtration and washed with water then dried under vacuum to give the title compound (5.23 g, 10.8 mmol). LC/MS: Rt=4.13, [MH]+ 485.

후처리

  1. temperatureThe reaction mixture was refluxed for 18 hours under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe reaction mixture triturated with water
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customthen dried under vacuum

출처 및 근거

ORD 기록
ord-eb2e70f17c5e40159395eb9eab2a6260
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207213B2

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