4-Toluenesulfonyl chloride → Oxetan-2-ylmethyl 4-methylbenzenesulfonate

HRID 78473Notes

Reaction equation

HRID 78473 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:6][CH2:5][O:4]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:17][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:1][CH2:2][CH:3]2[CH2:6][CH2:5][O:4]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12284142(Oxetan-2-yl)methanol

Product 1

HCID 13927594Oxetan-2-ylmethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxymethyloxetane (TCI-US, 2.0 g, 23 mmol) in 10 mL of CH2Cl2 and 10 mL of pyridine was added p-toluenesulfonyl chloride (6.5 g, 34 mmol) in portions over 15 minutes. The mixture was stirred at ambient temperature for 3 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 5 mL portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 70% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 243 (M+H)+, 260 (M+NH4)+.

Workup

  1. customwas quenched with 10 mL of saturated, aqueous NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with three 5 mL portions of CH2Cl2
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification via column chromatography (SiO2, 70% hexanes in ethyl acetate)

Sources & evidence

ORD record
ord-b45dcc64a0934decb4171dc94b7441bc
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

Loading…