Chlorotrimethylsilane → Diethyl hydroxy(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylphosphonate

HRID 1666486Notes

Reaction equation

HRID 1666486 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=[O:14])=[N:7][CH:8]=1.[P:20]([O:27]CC)([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23].C[Si](Cl)(C)C>>[OH:14][CH:13]([P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])[C:12]1[CH:15]=[CH:16][CH:17]=[C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:18])([F:1])[F:19])=[CH:8][N:7]=2)[CH:11]=1

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 31215Triethyl phosphiteHCID 866239163-(5-(Trifluoromethyl)pyridin-2-yloxy)benzaldehyde

Product 1

HCID 86623917Diethyl hydroxy(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylphosphonateYield 53.6%

Procedure

To an ethereal solution of 3-(5-(trifluoromethyl)pyridin-2-yloxy)benzaldehyde (1.6 g, 5.98 mmol) and LiClO4 (5 mL, 5 M solution in diethylether) was added triethyl phosphite (1.24 g, 7.48 mmol) and TMSCl (0.813 g, 7.48 mmol) at 0° C. The reaction mixture was allowed to reach RT and stirred for 10 min. The reaction was quenched by adding distilled water (10 mL), extracted with CH2Cl2, dried and concentrated to dryness. The residue was purified by column chromatography (1:1 EtOAc:Hexane) to afford pure title compound (1.3 g). 1H NMR (500 MHz, CDCl3): δ 1.2 (m, 6H), 2.9 (m, 1H), 4.0 (m, 4H), 5.0 (d, 1H, J=11 Hz), 7.0 (d, 1H, J=8.5 Hz), 7.1 (d, 1H, J=7.5 Hz), 7.3 (s, 1H), 7.4 (m, 1H), 7.8 (m, 1H), 8.4 (s, 1H).

Workup

  1. customto reach RT
  2. customThe reaction was quenched
  3. additionby adding
  4. distillationdistilled water (10 mL)
  5. extractionextracted with CH2Cl2
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography (1:1 EtOAc:Hexane)

Sources & evidence

ORD record
ord-2d4171fca3e44b86b15734846671a3cb
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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