[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:23])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH3:22])=[C:13]([S:19]C#N)[C:14]=2[CH3:18])[O:9]1.O.Cl>CCOCC>[CH3:7][C:8]1([CH3:23])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH3:22])=[C:13]([SH:19])[C:14]=2[CH3:18])[O:9]1Lithium aluminum hydride (2.65 g, 69.6 mM) was suspended in anhydrous ether (165 ml) under an atmosphere of argon with external cooling to 15° C. A solution of the thiocyanate (A) (8.6 g, 34.8 mM) in anhydrous ether (100 ml) was added dropwise during 30 minutes and the mixture was then heated under reflux for 30 minutes. The reaction mixture was cooled and ether (80 ml) was added. Water (80 ml) was then added cautiously dropwise followed by 2M hydrochloric acid (120 ml). The organic layer was separated and combined with a further extract. The combined organic phase was washed with saturated sodium bicarbonate solution and then with brine. Evaporation of the solvent gave 2,2,5,7-tetramethylchroman-6-thiol (B) as a clear oil which was used without further purification.
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