Cesium carbonate → HCID 23590003, compound

HRID 1609910Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:29]([O:31][C:32](=[O:37])[CH:33](Br)[CH2:34][CH3:35])[CH3:30]>CN(C=O)C.O.[Na+].[Cl-]>[CH2:29]([O:31][C:32](=[O:37])[CH:33]([O:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:21][CH:20]=1)[CH2:34][CH3:35])[CH3:30]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenol in dry DMF (3.0 mL) under argon was treated with Cs2CO3 (483 mg, 1.5 mmol) then 2-bromobutyric acid ethyl ester (350 μL, 2.4 mmol). The reaction mixture was stirred at 55° C. for 18 h, was allowed to cool to room temperature, diluted with H2O, saturated with NaCl, and partitioned with ethyl acetate. The organic layer was washed with NaHCO3 then brine, dried (Na2SO4), and concentrated in vacuo to give a yellow oil (394 mg). The product was purified by radial chromatography using a 1 mm plate and 0-2% ethyl acetate in CH2Cl2 to give a yellow oil (216 mg, 88%). 1H NMR (400 MHz, CDCl3) δ 1.07 (t, 3H, J=7.33 Hz), 1.22-1.26 (m, 3H), 1.91-1.99 (m, 2H), 2.37 (s, 3H), 2.96 (t, 2H, J=6.60 Hz), 4.18-4.25 (m, 5H), 4.44 (t, 1H, J=6.35 Hz), 6.81 (s, 4H), 7.42-7.48 (m, 3H), 7.98-8.00 (m, 2H); MS (ES) m/e 410.2 (M+1).

Workup

temperatureto cool to room temperature
custompartitioned with ethyl acetate
washThe organic layer was washed with NaHCO3
dry with materialbrine, dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bed3dea46472476fba862840f6f447b1
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982278B2

Reaction notes

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