Pivaloyl chloride → 4-(2,3-Epoxypropoxy)-6-pivaloyloxymethyl-indole
Reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>N1C=CC=CC=1>[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[C:12]([CH2:14][O:15][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
8.7 g. 4-(2,3-epoxypropoxy)-6-hydroxymethyl-indole (cf. the preparation of the starting material in Example 15) were dissolved in 50 ml. anhydrous pyridine. To this solution were added dropwise, while stirring and cooling to 5°-10° C., 5 ml. pivalic acid chloride, 1.5-2 hours after the ending of the addition, the reaction mixture was poured into ice water. The aqueous phase was extracted 3 or 4 times with diethyl ether. The ethereal extract was successively washed with 1 N sulfuric acid, a saturated aqueous solution of sodium bicarbonate and water, then dried, treated with active charcoal and fullers' earth and subsequently evaporated. The crude 4-(2,3-epoxypropoxy)-6-pivaloyloxymethyl-indole thus obtained (12.5 g.; about 100% of theory) was further reacted without further purification.