Ammonia → 3-Mercapto-3-methylhexan-1-ol
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C([S:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])C1C=CC=CC=1.N.CCO.Cl>CCOCC>[SH:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12]C([S:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])C1C=CC=CC=1.N.CCO.Cl>CCOCC>[SH:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12]At a temperature of −78° C. to a solution of 16.0 g (67.1 mmol) of (rac)-3-benzylsulfanyl-3-methyl-hexan-1-ol of step (c) in 200 ml of Et2O was added from a cylinder about 200 ml of NH3. Then pieces of Na (ca. 4.0 g) were added until the reaction mixture remained blue for more than 20 min. The blue colored mixture was allowed to warm up to room temperature overnight and EtOH was added until the blue color disappeared. The mixture was then acidified with about 2.7 M of HCl, and extracted three times with 150 ml of Et2O. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. Distillation of the crude product at reduced pressure (40 mbar/130° C.) gave 11.2 g (73%) of (rac)-3-mercapto-3-methyl-hexan-1-ol in form of a colorless oil.
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