Triethylamine → HCID 59296137, compound

HRID 2233561Notes

Reaction equation

HRID 2233561 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH2:22]O)=[C:12]([CH2:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:13]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.CS([Cl:35])(=O)=O>ClCCl>[Cl:35][CH2:22][C:11]1[O:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:13][C:12]=1[CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59296152HCID 59296152, compound

Product 1

HCID 59296137HCID 59296137, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g [2-(4-Methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazol-5-yl]-methanol were dissolved in 30 ml dichloromethane and cooled in an ice bath. 0.88 ml triethylamine were added, followed by the addition of 0.49 ml methanesulfonylchloride. The ice bath was removed and the resulting mixture stirred at room temperature over night. The reaction mixture was then washed with water and brine, dried over MgSO4 and the solvent removed in vacuo to obtain 2.5 g of 5-chloromethyl-2-(4-methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazole as an oil which was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice bath was removed
  3. washThe reaction mixture was then washed with water and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2da57ec631c74c2da5ca02c9883174e1
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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