Potassium bisulfate → 2-Ethoxycarbonyl-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthalene

HRID 963718Notes

Reaction equation

HRID 963718 reaction equation
O[CH:2]1[C:11]2[C:6](=[C:7]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1>[CH2:33]([O:32][C:30]([C:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][Si:13]([C:26]([CH3:27])([CH3:29])[CH3:28])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]=1)=[O:31])[CH3:34]

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 536494731-Hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 545044522-Ethoxycarbonyl-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthaleneYield 130.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (5.9 g) in toluene (100 ml) was added KHSO4 (2.0 g). The mixture was stirred for 1 hour under reflux, 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 2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthalene (7.4 g).

Workup

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

Sources & evidence

ORD record
ord-6b83f0b766bf447c96e93df607d9a2c4
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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