3,4-dihydro-2H-pyran → HCID 59296143, compound

HRID 2233559Notes

Reaction equation

HRID 2233559 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:19][OH:20])=[O:5])[CH3:2].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:19][O:20][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59296124HCID 59296124, compound

Product 1

HCID 59296143HCID 59296143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g 4-Hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-5-carboxylic acid ethyl ester were dissolved in 85 ml dichloromethane. 4.0 ml 3,4-dihydro-2H-pyran and 1.85 mg pyridinium p-toluenesulfonate were added and the reaction mixture stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=4:1=>1:1) to obtain 12.3 g 2-(4-Methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazole-5-carboxylic acid ethyl ester as an oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=4:1=>1:1)

Sources & evidence

ORD record
ord-6af38ca40f294c1f80a2255f8060fe04
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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