Reaction #1726681

Reaction equation

1B

(3-Hydroxyazetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Triethylamine

methane-sulfonyl chloride

→

1C

Yield 98.0%

1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Yield 98.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperaturewas cooled in an ice-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Otherthe cooling bath was removed
4. 4
   Othertransferred to a separatory funnel
5. 5
   WashThe mixture was washed with water
6. 6
   OtherThe organic solution was dried (phase separator)
7. 7
   Otherevaporated

Procedure

A suspension of 1B (2.00 g, 8.16 mmol) in dichloromethane (200 mL) was cooled in an ice-bath. Triethylamine (1.58 mL, 11.42 mmol) was added followed by methane-sulfonyl chloride (0.85 mL, 11.01 mmol). After the addition, the cooling bath was removed. The mixture was stirred overnight and then transferred to a separatory funnel. The mixture was washed with water and then with aqueous NaHCO3. The organic solution was dried (phase separator) and evaporated. There was obtained 2.58 g (98%) of 1C as a solid. 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 4.43 (dd, 1H), 4.64 (dd, 1H), 4.87 (dd, 1H), 5.12 (dd, 1H), 5.40 (m, 1H), 7.54 (t, 2H), 7.59 (t, 1H), 8.15 (d, 2H), MS (APCI+) m/z 324 [M+H]+.

Source