Diethyl Carbonate → 5-t-Butyldiphenylsilyloxy-2-ethoxycarbonyl-1-oxo-1,2,3,4-tetrahydronaphthalene

HRID 963716Notes

Reaction equation

HRID 963716 reaction equation
C(O[C:4](=[O:8])[O:5][CH2:6][CH3:7])C.[H-].[Na+].[Si:11]([O:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH2:31][CH2:32][CH2:33][C:34]2=[O:39])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Si:11]([O:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH2:31][CH2:32][CH:33]([C:4]([O:5][CH2:6][CH3:7])=[O:8])[C:34]2=[O:39])([C:24]([CH3:26])([CH3:27])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 224673025-Tert-butyldiphenylsilyloxy-1-tetralone

Product 1

HCID 540112435-t-Butyldiphenylsilyloxy-2-ethoxycarbonyl-1-oxo-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of diethylcarbonate (10.3 ml) and sodium hydride (4.2 g, 60% in oil) in toluene (300 ml) was added 5-t-butyldiphenylsilyloxy-1-oxo-1,2,3,4-tetrahydronaphthalene (17 g) at 100° C. The mixture was stirred for 4 hours at the same temperature and then the cooled solution was washed with sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 5-t-butyldiphenylsilyloxy-2-ethoxycarbonyl-1-oxo-1,2,3,4-tetrahydronaphthalene (20 g).

Workup

  1. washthe cooled solution was washed with sat. NaHCO3 and brine
  2. customThe dried solvent was evaporated in vacuo
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d29a4ae2a1e946ebb3381d9ba261c680
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

Loading…