Phosphorus oxychloride → Ethyl(4-methyl-2-phenyl-1,3-oxazol-5-yl)acetate

HRID 1454034Notes

Reaction equation

[C:1]([NH:9][CH:10]([CH3:19])[C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:19][C:10]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:18][C:11]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 90 °C

Procedure

To a crude mixture of ethyl 4-(benzoylamino)-3-oxopentanoate (0.6 g, 2.28 mmol) in DMF (4 mL) at rt was added POCl3(1.04 g, 6.84 mmol). The resulting solution was heated at 90° C. for 1 h, then cooled down to rt, and poured into ice for 30 minutes. The aqueous solution was carefully added to a saturated aqueous solution of NaHCO3. Phases were separated with EtOAc and the combined organic extracts were dried over MgSO4, and the solvent removed under reduced pressure. The crude material was purified on Biotage small column using a solvent gradient of 0 to 50% EtOAc/Hexane. Gave ethyl (4-methyl-2-phenyl-1,3-oxazol-5-yl)acetate (0.269 g 48% yield) as yellowish oil. ES-MS m/z 246.2 ((MH)+); HPLC RT (min) 2.77; 1H NMR (CDCl3) δ 8.01-7.98 (m, 2H), 7.45-7.41 (m, 3H), 4.20 (q, 2H), 3.71 (s, 2H), 2.21 (s, 3H), 1.28 (t, 3H).

Workup

temperaturecooled down to rt
additionpoured into ice for 30 minutes
customPhases were separated with EtOAc
dry with materialthe combined organic extracts were dried over MgSO4
customthe solvent removed under reduced pressure
customThe crude material was purified on Biotage small column

Sources & evidence

ORD record: ord-624c8ac674184b59a8498ec0e727ebac
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476742B2

Reaction notes

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