Triethyl phosphite → Diethyl 3-ethoxy-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylphosphonate

HRID 1666439Notes

Reaction equation

HRID 1666439 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:20][CH2:21][CH3:22])[CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=1.[CH2:23]([O:25][P:26]([O:30]CC)[O:27][CH2:28][CH3:29])[CH3:24]>>[CH2:21]([O:20][C:18]1[CH:19]=[C:3]([CH:4]=[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[CH:17]=1)[CH2:2][P:26](=[O:30])([O:27][CH2:28][CH3:29])[O:25][CH2:23][CH3:24])[CH3:22]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 668756612-(3-(Chloromethyl)-5-ethoxyphenoxy)-5-(trifluoromethyl)pyridine

Product 1

HCID 86623905Diethyl 3-ethoxy-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylphosphonateYield 82%

Conditions

Temperature
150 °C

Procedure

2-(3-(Chloromethyl)-5-ethoxyphenoxy)-5-(trifluoromethyl)pyridine from Step 3 was treated neat with triethylphosphite (0.30 mL, 1.75 mmol) and heated to 150° C. After 16 h, the reaction mixture was cooled and purified by silica gel chromatography (0-50%, EtOAc:CH2Cl2) to afford the title compound (400 mg, 82% yield) as a thick oil.

Workup

  1. temperaturethe reaction mixture was cooled
  2. custompurified by silica gel chromatography (0-50%, EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-b26673cc40314ff194b5616d877c670c
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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