4-Methanesulfonyl-butan-1-ol synthesis

Yield:26981-51-1 95%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 0 - 20; for 20 h;

Steps:

3 Referential Example 3: 4-(Methylsulfonyl)-1-butanol

Referential Example 3: 4-(Methylsulfonyl)-1-butanol While stirring under ice cooling, 3-chloroperbenzoic acid (3.04 g, 17.6 mmol) was added to a methylene chloride (100ml) solution of 4-(methylthio)-1-butanol (1.01 g, 8.40 mmol).. At room temperature, the mixture was stirred for 20 hours.. After completion of the reaction was confirmed, the solvent was concentrated under reduced pressure.. To the residue were added diethyl ether and water to separate the water layer.. The resulting water layer was concentrated under reduced pressure.. methylene chloride was added to the residue.. The mixture was dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure.. The residue was subjected to chromatography on a silica gel column.. From the fraction eluted with methanol:methylene chloride(=1:20), the title compound (1.21 g, 95%) was obtained as a pale yellow oil. IR (ATR) ν: 3494, 2931, 2877, 1457, 1413, 1282, 1122, 1054, 1029, 966, 827, 765, 518, 462 cm-1.1H-NMR (400MHz, CDCl3) δ: 1.55-1.91(3H,m), 1.91-2.11(2H,m), 2.92(3H,s), 3.09(2H,t,J=7.9Hz), 3.72(2H,t,J=6.1Hz). MS (m/z): 153 (M++H).

References:

EP1466898,2004,A1 Location in patent:Page 47