[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[S:9][C:10]([C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[C:11]([C:13](OC)=[O:14])[N:12]=1.O>C1COCC1>[CH3:7][C:8]1[S:9][C:10]([C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[C:11]([CH2:13][OH:14])[N:12]=1To a stirred suspension of lithium aluminiumhydride (139 mg, 3.64 mmol) in THF (5 mL) a solution of methyl 2-methyl-5-m-tolylthiazole-4-carboxylate [1007873-98-4] (600 mg, 2.43 mmol) in THF (5 mL) was added at −25° C. and stirred for 30 min. Then water (5 mL) was added dropwise and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (eluent: 50% ethyl acetate in hexane) to yield the title compound (300 mg, 56%). [LCMS RtF=0.32 min, [M+H]+=219.9; TLC Rf=0.20 (methanol/chloroform 10:90)].
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