Cesium carbonate → 4-[2-(2,6-Diallyl-4-benzyloxy-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazole

HRID 898460Notes

Reaction equation

HRID 898460 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([CH2:18][CH:19]=[CH2:20])[C:5]=1[OH:21])[CH:2]=[CH2:3].[CH3:22][C:23]1[O:27][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:25][C:24]=1[CH2:34][CH2:35]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([CH2:18][CH:19]=[CH2:20])[C:5]=1[O:21][CH2:35][CH2:34][C:24]1[N:25]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:27][C:23]=1[CH3:22])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonate2×HCID 219859512,6-Diallyl4-benzyloxyphenol

Product 1

HCID 222611564-[2-(2,6-Diallyl-4-benzyloxy-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazoleYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-diallyl-4-benzyloxy-phenol (520 mg, 1.85 mmol), toluene-4-sulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)ethyl ester (Japan Tobacco Inc WO 9518125) (828 mg, 2.32 mmol), and Cs2CO3 (604 mg, 1.85 mmol) was heated at 55° C. in DMF (5 mL) for 20 h. Additional toluene-4-sulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)ethyl ester (300 mg, 0.839 mmol) and Cs2CO3 (200 mg, 0.614 mmol) were added, and the mixture was heated for 18 h. The reaction mixture was cooled and partitioned between EtOAc (40 mL) and H2O (10 mL). The organic layer was washed with brine (15 mL), dried (Na2SO4), and concentrated. The crude product was purified by radial chromatography using hexanes:ethyl acetate (8:1) to give a colorless oil (722 mg, 83%): 1H NMR (400 MHz, CDCl3) δ 2.38 (s, 3H), 2.95 (t, 2H, J=6.3 Hz), 3.33 (d, 2H, J=6.3 Hz), 4.01 (t, 2H, J=6.3 Hz), 4.96 (s, 2H), 4.97-5.02 (m, 2H), 5.03 (s, 2H), 5.84-5.94 (m, 1H), 6.65 (s, 2H), 7.28-7.45 (m, 8H), 7.99 (dd, 2H, J=2.0, 7.8 Hz).

Workup

  1. temperaturethe mixture was heated for 18 h
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between EtOAc (40 mL) and H2O (10 mL)
  4. washThe organic layer was washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by radial chromatography

Sources & evidence

ORD record
ord-8561a93aeba142898aa5f21e5efe6d73
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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