Methane → HCID 69002356, compound

HRID 1987994Notes

Reaction equation

HRID 1987994 reaction equation
[CH3:1][C:2]([CH:5]=[O:6])([CH3:4])[CH3:3].[NH2:7][C:8]1[C:9](O)=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].C>>[C:2]([C:5]1[O:6][C:9]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=[CH:17][C:8]=2[N:7]=1)([CH3:4])([CH3:3])[CH3:1]

Participants

4

Reactant 3

HCID 297MethaneHCID 12417PivalaldehydeHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Product 1

HCID 69002356HCID 69002356, compoundYield 60%

Conditions

Temperature
120 °C

Procedure

A mixture of pivaldehyde (1.65 mL, 15.4 mmol), methyl 3-amino-2-hydroxybenzoate (501 mg, 3.0 mmol) and Darco KB-B (375 mg) in xylenes (8 mL) was heated under an oxygen atmosphere at 120° C. for 12 h. The reaction mixture was cooled to room temperature, filtered through a celite pad. The filtrate was concentrated and the crude material was purified by column chromatography (silica gel, 7:3 hexanes/ethyl acetate) to afford the desired methyl 2-tert-butylbenzoxazole-7-carboxylate (417 mg, 60%) as a light orange oil: 1H NMR (500 MHz, CDCl3) δ 7.94 (dd, J=7.8, 0.9 Hz, 1H), 7.88 (dd, J=7.8, 0.9 Hz, 1H), 7.36 (t, J=7.8 Hz, 1H), 4.01 (s, 3H), 1.54 (s, 9H); MS (ESI+) m/z 234 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated
  4. customthe crude material was purified by column chromatography (silica gel, 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e94986f6c6354b45a6eb81b1e398b8b5
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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