[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6]([CH:8]1[O:10][CH2:9]1)Cl.[OH-].[Na+].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>O.[Sn](Cl)(Cl)(Cl)Cl>[CH3:2][C:1]([CH3:4])([O:5][CH2:6][CH:8]([OH:10])[CH2:9][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:3]
A mixture of 100.0 g (1.35 m) of tert.butyl alcohol and 51.4 g (1.35 m) of epichlorohydrin in 240 ml of xylenes was stirred and heated to 50° C. Tin (IV) chloride (3.5 g; 1.6 ml; 0.031 m) was added all at once and the reaction mixture immediately exothermed to about 100° C. The reaction mixture was stirred at about 50° C. for 1.5 hrs then cooled to 5° C. while a mixture of 97 g of 50% sodium hydroxide solution and 195 g of ice was added followed by 115.1 g (1.62 m) of pyrrolidine. The reaction mixture was stirred and heated to reflux for 1 hr. The reaction mixture was cooled to RT, diluted with 1 liter of water and extracted with ether. The ether soluble portion was dried and concentrated in vacuo to give 92.4 g of oil which was distilled at 97.5°-97° C./0.075 mm to yield 63.85 g of the title compound.
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