Diethylamine → 2-Chloro-5-{[(oxan-2-yl)oxy]methyl}pyridine

HRID 1030027Notes

Reaction equation

HRID 1030027 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(NCC)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 8021DiethylamineHCID 80803,4-dihydro-2H-pyranHCID 312751,4-DioxaneHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 221273782-Chloro-5-{[(oxan-2-yl)oxy]methyl}pyridineYield 124.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 44.3 g of 6-chloro-3-pyridine-carbinol, 300 ml of dioxan and 104.3 g of 3,4-dihydro-2H-pyran was treated with 3 g of p-toluenesulfonic acid monohydrate and stirred at 55° C. for 2 hours. The reaction mixture was treated with 10 ml of diethylamine and, after cooling, taken up in diethyl ether. Repeated washing with water, drying over sodium sulfate and concentration in a vacuum yielded 87.3 g of crude 2-chloro-5-[(tetrahydro-2-pyranyloxy)methyl]pyridine.

Workup

  1. temperatureafter cooling
  2. washRepeated washing with water
  3. dry with materialdrying over sodium sulfate and concentration in a vacuum

Sources & evidence

ORD record
ord-c6469076aac347739cee08f1235dcbb5
Source dataset
uspto-grants-1992_04
Patent number
US05104569

Reaction notes

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