3,4-dihydro-2H-pyran → ethyl 2-[(tetrahydro-2H-pyran-2-yloxy)methyl]isonicotinate

HRID 450782Notes

Reaction equation

HRID 450782 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][N:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(OCC)(=O)C>ClCCl>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][N:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19744774Ethyl 2-(hydroxymethyl)pyridine-4-carboxylate

Product 1

HCID 59478246ethyl 2-[(tetrahydro-2H-pyran-2-yloxy)methyl]isonicotinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.64 g of ethyl 2-(hydroxymethyl)isonicotinate in 32.8 ml of dichloromethane were added 1.24 ml of dihydropyrane and 2.32 g of pyridinium p-toluenesulfonate, followed by stirring overnight. Ethyl acetate was added thereto, followed by washing with a saturated aqueous ammonium chloride solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 2.4 g of ethyl 2-[(tetrahydro-2H-pyran-2-yloxy)methyl]isonicotinate.

Workup

  1. washby washing with a saturated aqueous ammonium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e597701b0af46e89f0b10e3e45bea2e
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

Loading…