Triethylamine → HCID 22112806, compound

HRID 564717Notes

Reaction equation

HRID 564717 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[CH:11]=[C:10]([C:12]3(O)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[O:9][C:8]=12.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[O:15]1[CH2:14][CH:13]=[C:12]([C:10]2[O:9][C:8]3=[C:3]([O:2][CH3:1])[N:4]=[CH:5][CH:6]=[C:7]3[CH:11]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69963098HCID 69963098, compound

Product 1

HCID 22112806HCID 22112806, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(7-methoxyfuro[2,3-c]pyridin-2-yl)tetrahydopyran-4-ol (2.5 g) in dry dichloromethane (50 ml) was stirred at 0° C. under an atmosphere of dry nitrogen. Triethylamine (5.6 ml) was added followed by methanesulfonyl chloride (2.3 ml). The mixture was stirred overnight at room temperature. The solvent was removed in vacuo. Purification by column chromatography on silica eluting with 50% hexane in ethyl acetate gave 2-(3,6-dihydro-2H-pyran-4-yl)-7-methoxyfuro[2,3-c]pyridine (2.5 g) as a colourless oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification by column chromatography on silica eluting with 50% hexane in ethyl acetate

Sources & evidence

ORD record
ord-bd97fd1590dc4bed8edb94fbcd9c4dc4
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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