Tert-butyl 5-bromopentanoate → tert-Butyl delta-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerate

HRID 393866

반응식

HRID 393866 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH:13][C:14]1[C:15](=[O:25])[C:16]2[C:21]([C:22](=[O:24])[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2>C1C=CC=CC=1.[Ag]>[O:25]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]([O:24][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:23][C:14]1=[O:13]

참가 물질

5

반응물 2

HCID 545791Tert-butyl 5-bromopentanoateHCID 178516607HCID 178516607, 화합물

생성물 1

HCID 22647808tert-Butyl delta-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerate수율 30.3%

시약·촉매·용매 2

HCID 23954Silver촉매HCID 241Benzene용매

실험 절차

A mixture of tert-butyl 5-bromovalerate (1 g, 4.2 mmol) and the silver salt of 2-hydroxy-1,4-naphthoquinone (0.8 g, 3.84 mmol) in benzene (10 mL), was stirred for 24 h at 50° C. The reaction mixture was filtered through celite and the solvent was removed in vacuo. The residue was purified by flash chromatography (5% methanol in chloroform) to give a yellow solid (384 mg, 30%). 1H NMR (CDCl3) 8.12 (d, J=7.7 Hz, 1H), 7.89 (d, J=7.7 Hz, 1H), 7.70 (t, J=6.1 Hz, 1H), 7.59 (t, J=6.4 Hz, 1H), 5.95 (s, 1H), 4.17 (t, J=5.9 Hz, 2H), 2.35 (t, J=7.2 Hz, 2H), 1.90-2.05 (m, 2H), 1.78-1.90 (m, 2H), 1.47 (s, 9H).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash chromatography (5% methanol in chloroform)

출처 및 근거

ORD 기록
ord-0c822b9cf0ae4d7f8bc4196833db83bb
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809176B2

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