Pyridine → Oxetan-3-yl 2-isopropylthiobenzoate

HRID 1033213Notes

Reaction equation

HRID 1033213 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].C1(C)C=CC=CC=1.[OH:20][CH:21]1[CH2:24][O:23][CH2:22]1.N1C=CC=CC=1>O>[O:23]1[CH2:24][CH:21]([O:20][C:6](=[S:7])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[CH:1]([CH3:3])[CH3:2])[CH2:22]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140Toluene2×HCID 9942117Oxetan-3-olHCID 233531092-Isopropylthiobenzoyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.9 g of 2-isopropylthiobenzoic acid chloride and 20 ml of absolute toluene is added dropwise at a temperature of from 15° to 20° C. to a mixture of 4.44 g of 3-hydroxy-oxetane, 6.64 g of pyridine and 60 ml of absolute toluene. The resulting suspension is stirred for 2 hours at a temperature of from 20° to 25° C. and for a further 3 hours at a temperature of from 40° to 45° C. Water is added to the reaction mixture and the organic phase is washed with water, dried and concentrated by evaporation to yield 12.6 g of 2-isopropylthiobenzoic acid oxetan-3-yl ester in the form of a pale yellow oil.

Workup

  1. washthe organic phase is washed with water
  2. customdried
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c1ea6573314b42c7876515d98fc2f65f
Source dataset
uspto-grants-1994_05
Patent number
US05310722

Reaction notes

Loading…