p-Toluenesulfonic acid → HCID 22633460, compound

HRID 2417134Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][CH2:17][CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=CC=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[N:37]([CH:39]=[O:40])C>>[CH2:29]([O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][CH2:2][C:7]2[N:37]=[C:39]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:40][C:6]=2[CH3:5])=[CH:10][C:11]=1[CH2:16][CH2:17][CH3:18])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 4

HCID 6101p-Toluenesulfonic acid

HCID 6228Dimethylformamide

HCID 10796Cesium carbonate

HCID 222611274-(Benzyloxy)-2-propylphenol

Product 1

HCID 22633460HCID 22633460, compound

Conditions

Temperature: 55 °C

Procedure

A mixture of 4-benzyloxy-2-propylphenol (3.89 mmol), toluene-4-sulfonic acid 2-(5-methyl-2-biphenyl-4-yl-oxazol-4-ly) ethyl ester (4.67 mmol) (see Ex. 1, part F) and cesium carbonate (1.65 g 5.06 mmol) in anhydrous DMF (8 mL) was heated for 18 h at 55° C. The mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate (100 mL) and water (50 mL), washed with brine (50 mL), dried (Na2SO4), and removed in vacuo to give a crude oil which was purified using the Biotage FlashElute chromatography system using a 40 L normal phase cartridge, eluting with 10-15% ethyl acetate/hexanes to give 4-[2-(4-benzyloxy-3-propylphenoxy)ethyl]-5-methyl-2-phenyloxazole.

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was partitioned between ethyl acetate (100 mL) and water (50 mL)
washwashed with brine (50 mL)
dry with materialdried (Na2SO4)
customremoved in vacuo
customto give a crude oil which
customwas purified
washeluting with 10-15% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-117d579b48054af4a93d9f11e3ffbaf6
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825222B2

Reaction notes

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