3,4-dihydro-2H-pyran → Ethyl 6-(tetrahydropyran-2-yloxymethyl)-4-iodopyridine-2-carboxylate

HRID 1513994Notes

Reaction equation

HRID 1513994 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[C:5]([I:14])[CH:4]=1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C(Cl)Cl>[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[C:5]([I:14])[CH:4]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 68482661Ethyl 6-hydroxymethyl-4-iodopyridine-2-carboxylate

Product 1

HCID 68728025Ethyl 6-(tetrahydropyran-2-yloxymethyl)-4-iodopyridine-2-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2 (2.89 g, 9.4 mmol), 3,4-dihydro-2H-pyran (1.19 g, 14.1 mmol), pyridine p-toluenesulfonate (0.236 g, 0.94 mmol) and CH2Cl2 (50 ml) was stirred overnight at r.t. The solvent was evaporated and the product purified on silica gel (petroleum ether, by 40-60° C./ethyl acetate 2:5), yielding 3.18 g (86%) of the title compound.

Workup

  1. customThe solvent was evaporated
  2. customthe product purified on silica gel (petroleum ether, by 40-60° C./ethyl acetate 2:5)

Sources & evidence

ORD record
ord-fc24e1a6ed1c48e3b23ea053b6e21308
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

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