Water → O-ethyl O-(2,2,3,3,4,4-hexafluorocyclopentyl) S-propyl thiophosphate

HRID 373483Notes

Reaction equation

[F:1][C:2]1([F:12])[C:6]([F:8])([F:7])[C:5]([F:10])([F:9])[CH2:4][CH:3]1[OH:11].C([Li])CCC.[P:18](Cl)([S:23][CH2:24][CH2:25][CH3:26])([O:20][CH2:21][CH3:22])=[O:19].O>O1CCCC1.CCCCCC>[P:18]([S:23][CH2:24][CH2:25][CH3:26])([O:11][CH:3]1[CH2:4][C:5]([F:9])([F:10])[C:6]([F:7])([F:8])[C:2]1([F:12])[F:1])([O:20][CH2:21][CH3:22])=[O:19]

Participants

Conditions

Temperature: -20 °C

Procedure

4 g (0.02 mol) of 2,2,3,3,4,4-hexafluorocyclopentan-1-ol, dissolved in 50 ml of tetrahydrofuran, are treated, at -70° C., with 8 ml of a 2.5-molar butyllithium solution in hexane. The mixture is heated to -20° C. and 5 g (0.02 mol) of O-ethyl S-propyl chlorothiophosphate are then added dropwise. To complete the reaction, the mixture is stirred for 24 hours at 20° C., a little water is added to the reaction mixture, and the mixture is filtered through silica gel. After the solvent has been distilled off and the residue has been distilled, 1.6 g (22% of theory) of O-ethyl O-(2,2,3,3,4,4-hexafluorocyclopentyl) S-propyl thiophosphate of a boiling point of b.p.0.15 90°-92° C. are obtained.

Workup

customthe reaction
filtrationthe mixture is filtered through silica gel
distillationAfter the solvent has been distilled off
distillationthe residue has been distilled

Sources & evidence

ORD record: ord-0ba86778f75946efa8f867fd53c1e25f
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05164383

Reaction notes

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