Pyridine → Oxetan-3-yl 2-isopropylthiobenzoate

HRID 248290Notes

Reaction equation

HRID 248290 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[S:7])([CH3:3])[CH3:2].[OH:13][CH:14]1[CH2:17][O:16][CH2:15]1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:13][CH:14]1[CH2:17][O:16][CH2:15]1)=[S:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9942117Oxetan-3-olHCID 233531092-Isopropylthiobenzoyl chloride

Product 1

HCID 22407619Oxetan-3-yl 2-isopropylthiobenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 12.9 g of 2-isopropylthiobenzoyl chloride and 20 ml of absolute toluene is added dropwise to a mixture of 4.44 g of 3-hydroxyoxetane, 6.64 g of pyridine and 60 ml of absolute toluene at a temperature of 15° to 20° C. The suspension formed is stirred at a temperature of 20°-25° C. for 2 hours and at a temperature of 40°-45° C. for a further 3 hours. Adding water to the reaction mixture, washing the organic phase with water and drying and evaporating it gives 12.6 g of oxetan-3-yl 2-isopropylthiobenzoate as a pale yellow oil.

Workup

  1. customThe suspension formed
  2. washAdding water to the reaction mixture, washing the organic phase with water
  3. customdrying
  4. customevaporating it

Sources & evidence

ORD record
ord-d8712a1c2e814996baab8199a1536bc7
Source dataset
uspto-grants-1993_05
Patent number
US05209771

Reaction notes

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