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

HRID 963722
Notes
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Reaction equation

HRID 963722 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8071
1,2-Dimethoxyethane
Solvent

Procedure

To a solution of diethylphosphoric 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-butyldiphenylsilyloxy-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 into 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
  3. dry with materialHCl solution, sat. NaHCO3, and brine, dried 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
  8. dry with materialHCl solution, sat. NaHCO3, and brine, dried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-09361a74f47440ec8bad1f796cb71bb4
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05763489

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes