Hydrochloric Acid → HCID 68997793, compound

HRID 1987995Notes

Reaction equation

HRID 1987995 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([C:5]1[O:6][C:7]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69002356HCID 69002356, compound

Product 1

HCID 68997793HCID 68997793, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of methyl 2-tert-butylbenzoxazole-7-carboxylate (0.41 g, 1.77 mmol), lithium hydroxide monohydrate (222 mg, 5.30 mmol) and tetrahydrofuran/water (5:1, 6 mL) was stirred at room temperature for 17 h. The reaction mixture was cooled to 0° C., adjusted to pH 2 using 1 N HCl, and then extracted with dichloromethane (2×200 mL). The combined organic phase was washed with brine (2×50 mL), dried (Na2SO4), filtered and concentrated to afford the desired 2-tert-butylbenzoxazole-7-carboxylic acid (336 mg, 86%) as a pink solid: 1H NMR (300 MHz, DMSO-d6) δ 13.20 (br s, 1H), 7.95 (d, J=7.8 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.45 (t, J=7.8 Hz, 1H), 1.45 (s, 9H); MS (ESI+) m/z 220 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with dichloromethane (2×200 mL)
  3. washThe combined organic phase was washed with brine (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-04a88992689e4870a58a19738ab542af
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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