Réaction #1538307

Équation de réaction

Methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoate

methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoate

(1R)-(+)-camphor

LAH

→

[(3-tert-Butyldimethylsilyloxy-4-methoxyphenyl) methoxymethylene](1',7',7'-trimethyl bicyclo[2.2.1]heptane)

Solvants

tetrahydrofuran

THF

Conditions de réaction

Traitement

1. 1
   AutreThe product was purified on a preparative TLC plate (silica gel)
2. 2
   workup.ADDITIONDevelopment with hexane/ethyl acetate (10:1)gave the title compound as a mixture of two isomers (58 mg)

Mode opératoire

Methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoate (170 mg, 0.57 mmol, prepared in Example 1, Step 2 above) and (1R)-(+)-camphor (Aldrich, 120 mg, 0.79 mmol) were mixed and dissolved in anhydrous tetrahydrofuran (THF, 1.98 ml) and coupled as described in the procedure of Example 1, Step 3, above, by using titanium trichloride (1.9 g, 12.32 mmol), LAH (0.22 g, 5.80 mmol) and THF (13.8 ml). The product was purified on a preparative TLC plate (silica gel). Development with hexane/ethyl acetate (10:1)gave the title compound as a mixture of two isomers (58 mg). NMR(δ): 0.18 (s, 6H), 1.00 (s, 15H), 1.29 (s, 3H), 3.23 (s, 1H, minor isomer), 3.30 (s, 2H, major isomer), 3.85 (s, 3H).

Source