Water → 5-t-Butyldiphenylsilyloxy-1-ethoxycarbonylmethyl-3,4-dihydronaphthalene

HRID 344051Notes

Reaction equation

HRID 344051 reaction equation
[H-].[Na+].[Si:3]([O:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][CH2:24][CH2:25][C:26]2=O)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33].O>C(COC)OC>[Si:3]([O:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][CH2:24][CH:25]=[C:26]2[CH2:33][C:32]([O:35][CH2:36][CH3:37])=[O:34])([C:16]([CH3:19])([CH3:17])[CH3:18])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 224673025-Tert-butyldiphenylsilyloxy-1-tetralone

Product 1

HCID 538675035-t-Butyldiphenylsilyloxy-1-ethoxycarbonylmethyl-3,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of diethyiphosphoric acid ethyl ester (19 g) in dimethoxyethane (200 ml) was added NaH (3.4 g, 60%) in oil) at 0° C. under N2. After being stirred for 30 minutes, 5-t-butyidiphenylsilyloxy-1-oxo-1,2,3,4-tetrahydronaphthalene (20 g) was added to the mixture. After being stirred for 12 hours at 80° C., the solution was poured hnto a mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was dissolved into a mixture of toluene (100 ml and 1,8-diazabicyclo[5.4.0]-7-undecene (17 ml) and the mixture was stirred for 3 days at 100° C. The solution was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 5-t-butyldiphenylsilyloxy-1-ethoxycarbonylmethyl-3,4-dihydronaphthalene (20.3 g).

Workup

  1. stirringAfter being stirred for 12 hours at 80° C.
  2. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved into a mixture of toluene (100 ml and 1,8-diazabicyclo[5.4.0]-7-undecene (17 ml)
  6. stirringthe mixture was stirred for 3 days at 100° C
  7. washThe solution was washed with 1N-HCl solution, sat. NaHCO3, and brine
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-72aac727b76e4e83bc7bdc14ab529ea2
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

Loading…