Dimethyl Sulfide → Tert-butyl 3-(hydroxymethyl)-5-methylnonanoate

Reaction equation

[BH3:23].[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([CH2:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12][CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH3:18])=[O:19].[CH2:24]1[O:25][CH2:26][CH2:27][CH2:28]1.[CH3:20][S:21][CH3:22]>>[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([CH2:7][CH:8]([CH2:9][OH:10])[CH2:12][CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH3:18])=[O:19]