1-Bromonaphthalene → 1,1-Diethoxy-1,2-dihydrocyclobuta[a]naphthalene

HRID 2229435Notes

Reaction equation

HRID 2229435 reaction equation
[NH2-].[Na+].O1CCCC1.Br[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[CH2:19]([O:21][C:22]([O:24][CH2:25][CH3:26])=[CH2:23])[CH3:20]>O.CCOCC>[CH2:19]([O:21][C:22]1([O:24][CH2:25][CH3:26])[C:9]2=[C:18]3[C:13](=[CH:12][CH:11]=[C:10]2[CH2:23]1)[CH:14]=[CH:15][CH:16]=[CH:17]3)[CH3:20]

Participants

7

Reactant 4

HCID 70011-BromonaphthaleneHCID 8028TetrahydrofuranHCID 24533Sodium amideHCID 1376731,1-Diethoxyethene

Product 1

HCID 184677931,1-Diethoxy-1,2-dihydrocyclobuta[a]naphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

9.4 g of sodium amide are introduced into 350 ml of tetrahydrofuran. 25.9 g of 1-bromonaphthalene and 28 g of freshly prepared 1,1-diethoxyethylene are poured in succession into that mixture. The reaction mixture is refluxed for 16 hours and than taken up in water and ether. After washing the organic phase to neutral pH and drying thereof, the expected product is isolated and chromatographed over silica gel (dichloromethane/cyclohexane: 1/1).

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. washAfter washing the organic phase to neutral pH
  3. customdrying

Sources & evidence

ORD record
ord-1b0510dcb64a474a98ea830319b4c1d8
Source dataset
uspto-grants-2002_07
Patent number
US06420413B2

Reaction notes

Loading…