Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol → Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

HRID 2375741Notes

Reaction equation

HRID 2375741 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[O:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:21][CH:20]=1)[OH:18]>C(Cl)Cl>[O:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:23][CH:24]=1)=[O:18]

Participants

4

Reactant 2

HCID 59855140Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 59855138Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanoneYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PCC (14.5 mmol, 20% w/w on silica gel) was added to a solution of 10.1 (2.91 mmol) in DCM (20 mL). After 1 hour, the reaction mixture was chromatographed (silica gel, 1:2 EtOAc/hexane) to obtain compound 10.2 (2.41 mmol). MS ESI (pos.) m/e:296.0 (M+Na). 1H NMR (500 MHz) (DMSO-d6) δ 8.52 (s, 1H); 8.43 (d, J=9 Hz, 2H); 7.67 (s, 1H); 7.23 (d, J=9 Hz, 2H); 5.71 (m, 1H); 3.74-3.76 (m, 1H); 3.62-3.65 (m, 1H); 1.88-1.91 (m, 2H); 1.81-1.82 (m, 1H); 1.59-1.67 (m, 3H).

Workup

  1. customthe reaction mixture was chromatographed (silica gel, 1:2 EtOAc/hexane)

Sources & evidence

ORD record
ord-344f0c3150ce4b6f814d3f8f8159f174
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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