p-Toluenesulfonic acid monohydrate → HCID 66815740, compound

HRID 2367927Notes

Reaction equation

HRID 2367927 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>CO>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21226206Ethyl acetate hexaneHCID 66815652HCID 66815652, compound

Product 1

HCID 66815740HCID 66815740, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 6-(3-(6-(tetrahydro-2H-pyran-2-yloxy)hexyloxy)phenyl) picolinate (12), (260 mg, 0.63 mmol) in methanol (1 mL) was added catalytic p-toluenesulfonic acid monohydrate (26 mg) and the mixture was stirred at RT for 2-4 h. The reaction was monitored by TLC (ethyl acetate:hexane 1:1). After completion the volatiles were removed in vacuo and the oily residue dissolved in ethyl acetate. The solution was washed with bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by gradient flash chromatography (ethyl acetate:hexane) to provide 135 mg (65%) of 13. TLC Rf=0.34 (ethyl acetate:hexanes 1:1), MS m/z 330 (M+H)+

Workup

  1. customAfter completion the volatiles were removed in vacuo
  2. dissolutionthe oily residue dissolved in ethyl acetate
  3. washThe solution was washed with bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by gradient flash chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-032bf06ef2fc4139984137dd3474e03b
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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