Phosphorus oxychloride → HCID 19764418, compound

HRID 1885482Notes

Reaction equation

HRID 1885482 reaction equation
[F:1][C:2]([F:23])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([CH3:6])(O)[CH3:4].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[F:1][C:2]([F:23])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([CH3:6])=[CH2:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 19764370HCID 19764370, compound

Product 1

HCID 19764418HCID 19764418, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 160 mg of 3,3-difluoro-2-methyl-2-nonadecanol in 2 ml of pyridine containing 50 ul of phosphorous oxychloride is heated at 90° C. then allowed to cool to 50° C. An additional 250 ul of phosphorous oxychloride is added followed by heating at 90° C. for 2 hours. After allowing to stand at ambient temperature for 18 hours, the volatiles are removed and the concentrate partitioned between hexanes and 10% hydrochloric acid. The organic layer is washed with water and 10% sodium bicarbonate then dried and evaporated to a residue which is purified by chromatography on silica gel using hexane to give 140 mg of the desired product as an oil.

Workup

  1. temperatureby heating at 90° C. for 2 hours
  2. customthe volatiles are removed
  3. customthe concentrate partitioned between hexanes and 10% hydrochloric acid
  4. washThe organic layer is washed with water and 10% sodium bicarbonate
  5. customthen dried
  6. customevaporated to a residue which
  7. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-39f7931ae2cf4e4b9d9a103c42fff79f
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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