Benzyl 5-bromopentanoate → Benzyl 5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerate

HRID 393867Notes

Reaction equation

HRID 393867 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[OH:16][C:17]1[C:18](=[O:28])[C:19]2[C:24]([C:25](=[O:27])[CH:26]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2>C1C=CC=CC=1.[Ag]>[O:28]=[C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]([O:27][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:26][C:17]1=[O:16]

Participants

5

Reactant 2

HCID 562251Benzyl 5-bromopentanoateHCID 178516607HCID 178516607, compound

Product 1

HCID 22647819Benzyl 5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerate

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 241BenzeneSolvent

Procedure

A mixture of benzyl 5-bromovalerate (2.27 g, 8.4 mmol) and the silver salt of 2-hydroxy-1,4-naphthoquinone (1.63 g, 5.81 mmol) in benzene (8 mL) was stirred for 48 h at 55° C. and filtered through celite. The filtrate was diluted with diethyl ether, extracted with a 20% aqueous solution of NaHSO3 then basified to pH 10-11 with Na2CO3, and extracted with CH2Cl2. Yellow solid (1.334 g, 63%). 1H NMR (CDCl3) 8.12 (d, J=7.5 Hz, 1H), 7.85 (d, J=7.7 Hz, 1H), 7.68 (t, J=7.5, 1H), 7.58 (t, J=7.7 Hz, 1H), 7.25-7.50 (m, 5H), 5.93 (s, 1H), 5.14 (s, 2H), 4.15 (t, J=5.7 Hz, 2H), 2.50 (t, J=7.0 Hz, 2H), 1.8-2.2 (m, 4H).

Workup

  1. filtrationfiltered through celite
  2. additionThe filtrate was diluted with diethyl ether
  3. extractionextracted with a 20% aqueous solution of NaHSO3
  4. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-bb94f2fc53f343eda07349bf34b93fb0
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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