Reaction #476622

Reaction equation

NaHCO3

1,4-dioxaspiro[4.5]decan-8-ol

triethylamine

methanesulfonyl chloride

→

title compound

Yield 98.8%

1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate

Yield 98.8%

Solvents

DCM

Conditions

Workup

1. 1
   workup.ADDITIONadded dropwise under an atmosphere of nitrogen
2. 2
   Extractionextracted with DCM (2×50 mL)
3. 3
   WashThe extracts were washed with brine (50 mL)
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Otherleaving a beige oil which
7. 7
   Otherwas recrystallized from hexanes (22 mL)

Procedure

A solution of 1,4-dioxaspiro[4.5]decan-8-ol (1.10 g, 6.81 mmol), triethylamine (1.21 mL, 8.67 mmol) in DCM (25.2 mL) was cooled in an ice/water bath and treated with methanesulfonyl chloride (675 μL, 8.67 mmol) added dropwise under an atmosphere of nitrogen. The mixture was stirred at 25° C. overnight. The mixture was treated with saturated aqueous NaHCO3 (20 mL) and extracted with DCM (2×50 mL). The extracts were washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo leaving a beige oil which was recrystallized from hexanes (22 mL) to give 1.59 g (98%) of the title compound as a white crystalline solid. 1H NMR (400 MHz, CDCl3) δ 1.61-1.68 (m, 2H), 1.82-1.90 (m, 2H), 1.94-2.08 (m, 4H), 3.02 (s, 3H), 3.91-4.00 (m, 4H), 4.82-4.88 (m, 1H); MS (ESI): 237.10 [M+H]+; HPLC tR=2.54 min.

Source