Water → 4-(4-Nitrobenzyl)-2-(trifluoromethyl)pyridine

HRID 729946Notes

Reaction equation

HRID 729946 reaction equation
C(OC(=O)[CH:5]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)C.O.[Li+].[OH-]>CO>[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([C:12]([F:15])([F:13])[F:14])[CH:7]=2)=[CH:21][CH:20]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57833537HCID 57833537, compound

Product 1

HCID 578333894-(4-Nitrobenzyl)-2-(trifluoromethyl)pyridineYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product prepared in Step 1 (440 mg, 1.24 mmol) in methanol (13 mL) containing a drop of water, was added powdered LiOH (36 mg, 1.5 mmol) and the mixture was stirred at rt overnight. The mixture was concentrated to remove the methanol, diluted in dichloromethane, and washed with water. The combined organic extracts were dried over sodium sulfate, concentrated in vacuo, and purified by column chromatography eluting with 10-25% ethyl acetate in hexanes to give 4-(4-nitrobenzyl)-2-(trifluoromethyl)pyridine as a light yellow solid (100 mg, 29%). 1H NMR (CHCl3-d) δ 8.65 (d, J=4.7 Hz, 1H), 8.21 (m, 2H), 7.49 (s, 1H), 7.35 (m, 2H), 7.28 (m, 1H), 4.18 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the methanol
  3. additiondiluted in dichloromethane
  4. washwashed with water
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography
  8. washeluting with 10-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0ac5a7f56aed490ea5caec372817d5bb
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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