3,4-dihydro-2H-pyran → 2-Chloro-5-{[(oxan-2-yl)oxy]methyl}pyridine

HRID 486366Notes

Reaction equation

HRID 486366 reaction equation
[CH:1]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]=[C:3]([Cl:9])[CH:2]=1.O1CCOCC1.[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(OCC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:9][C:3]1[CH:2]=[CH:1][C:6]([CH2:7][O:8][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][O:16]2)=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 221273782-Chloro-5-{[(oxan-2-yl)oxy]methyl}pyridineYield 113.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 85 g of 6-chloro-3-pyridinecarbinol, 800 ml of dioxan and 129.8 g of 3,4-dihydro-2H-pyran was treated with 5.7 g of p-toluenesulphonic acid monohydrate, stirred at room temperature for 0.75 hours and subsequently at 65° C. for 2.75 hours. The reaction mixture was treated with 15 ml of triethylamine and, after cooling, taken up in diethyl ether. Repeated washing with saturated sodium chloride solution, drying over sodium sulphate and evaporation yielded 153.2 g of crude 2-chloro-5-[(tetrahydro-2-pyranyloxy)methyl]pyridine as a brown-red oil.

Workup

  1. temperatureafter cooling
  2. washRepeated washing with saturated sodium chloride solution
  3. dry with materialdrying over sodium sulphate and evaporation

Sources & evidence

ORD record
ord-cf59d45d557b412dbf48bb7504fdecf0
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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