[H-].[Na+].[CH3:3][O:4][CH:5]([O:12][CH3:13])[CH2:6][CH:7]([CH2:10][OH:11])[CH2:8][OH:9].[H][H].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.C1COCC1.C(O)C>[CH2:16]([O:9][CH2:8][CH:7]([CH2:6][CH:5]([O:4][CH3:3])[O:12][CH3:13])[CH2:10][O:11][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Sodium hydride (55% in oil, 32.72 g, 0.75 mol) was washed twice with n-hexane and suspended in 200 ml of THF. 4,4-Dimethoxy-2-(hydroxymethyl)butanol (49.26 g, 0.3 mol) was added dropwise to maintain a gentle evolution of hydrogen gas. Then benzyl chloride (94.94 g, 0.45 mol) was added during 30 min. and the mixture was refluxed over-night, cooled, diluted with 50 ml of ethanol, and evaporated in vacuum. The residue was suspended in about 200 ml of water and extracted with 3×100 ml of ether. The combined organic extracts were dried (MgSO4) and distilled in vacuum. The title compound (94.34 g, 91%) was obtained at 197°-200° C. (0.01 mm Hg).
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