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

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).

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

ORDレコード

ord-09361a74f47440ec8bad1f796cb71bb4

出典データセット

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05763489