Sodium Hydroxide → HCID 22261210, compound

HRID 1609965Notes

Reaction equation

C([O:3][C:4](=[O:30])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:9]([CH2:28][CH3:29])[CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH2:28]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:19][C:20]=1[CH3:21])[O:6][CH2:5][C:4]([OH:30])=[O:3])[CH3:29]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of {3-ethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}acetic acid ethyl ester (0.23 g, 0.57 mmol) in ethanol (10 mL) was treated with 2.5 N aqueous NaOH (1.1 mL), and heated at 55° C. for 2 h. The reaction was cooled to ambient temperature and concentrated down to near dryness. The residue was then diluted with EtOAc (40 mL) and water (20 mL) and acidified to pH=1 with 1N aqueous HCl. The organic layer was washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give a white solid (0.18 g, 81%). 1H NMR (400 MHz, CDCl3) δ 7.98 (dd, J=7.8, 2.9 Hz, 2H), 7.46-7.40 (m, 3H), 6.79 (d, J=2.9 Hz, 1H), 6.70 (d, J=8.8 Hz, 1H), 6.63 (dd, J=8.8, 2.9 Hz, 1H), 4.58 (s, 2H), 4.14 (t, J=6.4 Hz, 2H), 3.01 (t, J=6.4 Hz, 2H), 2.56 (q, J=7.5 Hz, 2H), 2.39 (s, 3H), 1.11 (t, J=7.6 Hz, 3H); MS (ES) m/e 382 (M+1).

Workup

temperatureThe reaction was cooled to ambient temperature
concentrationconcentrated down to near dryness
additionThe residue was then diluted with EtOAc (40 mL) and water (20 mL)
washThe organic layer was washed with brine (20 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-08cc860fe90844278aef7ec19663c571
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982278B2

Reaction notes

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