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

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).

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

ORDレコード

ord-72aac727b76e4e83bc7bdc14ab529ea2

出典データセット

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05863918