Water → (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask was placed (R)-(tetrahydro-furan-2-yl)-methanol (prepared as in PCT WO 2003/095438 A1, Example 3, 4.65 g, 45.5 mmol), methylene chloride (100 mL) and triethylamine (8.4 mL, 60.6 mmol) and it was cooled to 0° C. To this cooled solution was then added a solution of p-toluenesulfonyl chloride (10.4 g, 54.6 mmol) in methylene chloride (30 mL) dropwise. Once the addition was complete the reaction was then warmed to 25° C. and stirred for 16 h. The reaction was then diluted with water (50 mL) and extracted with methylene chloride (3×30 mL). The combined organic extracts were then dried over sodium sulfate, filtered and concentrated in vacuo. Purification on an AnaLogix Intelliflash system (80 g column, 3% ethyl acetate/hexanes to 40% ethyl acetate/hexanes) afforded toluene-4-sulfonic acid tetrahydro-furan-2(R)-ylmethyl ester (8.37 g, 72%) as a clear colorless oil: [α]32589=−14.4° (c=0.72, methylene chloride); ES-HRMS m/e calcd for C12H16O4S (M+H)+ 257.0842, observed 257.0841; 1H NMR (300 MHz, CDCl3) δ ppm 1.95-2.08 (m, 1H, CH of CH2), 2.14-2.40 (m, 3H, CH2 and CH of CH2), 4.02-4.19 (m, 2H, OCH2), 4.29-4.49 (m, 3H, OCH and OCH2), 7.69 (d, J=8.0 Hz, 2H, Ar), 8.15 (d, J=8.0 Hz, 2H, Ar).

Provenance & Evidence