tetrahydrothiopyran-3-carboxaldehyde synthesis

Yield: 35%

Reaction Conditions:

with hydrogen;Raney Ni in ethyl acetate at 60; under 2585.81 Torr; for 2 h;Inert atmosphere;

Steps:

97
Intermediate 97: Tetrahydro^H-thiopyran-S-carbaldehyde.CHOA mixture of 5,6-dihydro-2H-thiopyran-3-carbaldehyde (7.00 g, 0.055 mol) and Raney Ni (1.00 g) in Et₂OAc was stirred at 60 ⁰C under H₂ (50 psi) for 12 h. The catalyst was filtered off, and the filtrate was purified by chromatography eluting with a mixture of PE:EA (30:1 ), giving 2.50 g (35%) of the title compound.¹H NMR (CDCI₃) δ 1.40-1.55 (m, 1 H), 1.70-1.73 (m, 1 H), 1.94-2.02 (m, 2H), 2.50-2.54 (m, 3H), 2.55-2.65 (m, 1 H), 2.78-2.82 (m, 1 H), 9.57 (s, 1 H).

References:

SMITHKLINE BEECHAM CORPORATION WO2008/118724, 2008, A1 Location in patent:Page/Page column 120