p-Toluenesulfonic acid → HCID 86659815, compound

HRID 1846352Notes

Reaction equation

HRID 1846352 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyran2×HCID 7894146-Hydroxymethyl-nicotinic acid methyl ester

Product 1

HCID 86659815HCID 86659815, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 6-(hydroxymethyl)nicotinate (1.0 g, 6.0 mmol), 2,3-dihydropyran (1.5 mL, 16.5 mmol), and p-TsOH (1.14 g, 6.0 mmol) were combined in CH2Cl2 (100 mL) and stirred at room temperature for 18 hours. An additional 1 mL of 2,3-dihyropyran was added and the reaction was continued at room temperature for 24 hours. The reaction mixture was washed with water (200 mL), dried (MgSO4), filtered, and concentrated, to afford methyl 6-((tetrahydro-2H-pyran-2-yloxy)methyl)nicotinate (1.5 g, quantitative).

Workup

  1. waitthe reaction was continued at room temperature for 24 hours
  2. washThe reaction mixture was washed with water (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b474f4972b34404aa783e8e0d97190f3
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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