Oxetan-2-ylmethyl 4-methylbenzenesulfonate → HCID 59840935, compound

HRID 424762Notes

Reaction equation

HRID 424762 reaction equation
S(O[CH2:12][CH:13]1[CH2:16][CH2:15][O:14]1)(C1C=CC(C)=CC=1)(=O)=O.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C=O)C>[C:17]1(=[O:27])[N:21]([CH2:12][CH:13]2[CH2:16][CH2:15][O:14]2)[C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12

Participants

4

Reactant 2

HCID 13927594Oxetan-2-ylmethyl 4-methylbenzenesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 59840935HCID 59840935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-(tosyloxymethyl)oxetane (27 g, 111.4 mmol) (prepared according to A. O. Fitton et al., Synthesis 1987, (12), 1140-2) and potassium phtalimide (20.64 g, 111.4 mmol) in DMF (200 ml) is stirred at a temperature of 120° C. for 18 hours, then evaporated in vacuo. The residue is taken up in ethyl acetate, the organic layer washed with water and brine, dried (Na2SO4), filtered, and evaporated to dryness. The crude solid product (19.8 g, 82%) is used in the next step without further purification.

Workup

  1. customevaporated in vacuo
  2. washthe organic layer washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude solid product (19.8 g, 82%) is used in the next step without further purification

Sources & evidence

ORD record
ord-c72bef309ca84da2be1ea59c7b8f74f8
Source dataset
uspto-grants-2012_01
Patent number
US08106075B2

Reaction notes

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