Methanol → HCID 67983727, compound

HRID 330745Notes

Reaction equation

HRID 330745 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH2:5][S:6][C:7](=O)[CH3:8].CO.[CH3:18][O:19][C:20]([C:22]1C(CBr)=[CH:26][CH:25]=[CH:24][N:23]=1)=[O:21].C(OC(=O)C)C.C1CCCCC1>O>[CH3:18][O:19][C:20]([C:22]1[C:8]([CH2:7][S:6][CH2:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=2[C:2]([F:15])([F:14])[F:1])=[CH:26][CH:25]=[CH:24][N:23]=1)=[O:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 21867204Cyclohexane ethylacetateHCID 25099108Methyl 3-(bromomethyl)pyridine-2-carboxylateHCID 86700558HCID 86700558, compound

Product 1

HCID 67983727HCID 67983727, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of thioacetic acid S-(2-trifluoromethyl-benzyl)ester (10.2 g, 37.5 mmol) in methanol (130 ml) potassium carbonate (5.18 g, 37.5 mmol) was added at room temperature and it was stirred for 30 min. 3-Bromomethyl-pyridine-2-carboxylic acid methyl ester (4.40 g, 18.7 mmol) was added and after refluxing for 150 min the solution was diluted with water, extracted with ethylacetate, the organic phase dried with sodium sulfate and concentrated. Chromatography over silica with ethylacetate/cyclohexane gave 7.82 g colorless crystals (18.7 mmol).

Workup

  1. temperatureafter refluxing for 150 min the solution
  2. extractionextracted with ethylacetate
  3. dry with materialthe organic phase dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cda7f11bc0f547278685aaea9a341ae8
Source dataset
uspto-grants-2014_11
Patent number
US08877683B2

Reaction notes

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