Water → 1-(Benzo[d]oxazol-5-yl)cyclopropanecarboxylic acid

HRID 1847678Notes

Reaction equation

HRID 1847678 reaction equation
C[O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]=[N:13][C:12]=3[CH:16]=2)[CH2:7][CH2:6]1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].O>CCS>[O:15]1[C:11]2[CH:10]=[CH:9][C:8]([C:5]3([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]3)=[CH:16][C:12]=2[N:13]=[CH:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 591292661-Benzooxazol-5-yl-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 591293171-(Benzo[d]oxazol-5-yl)cyclopropanecarboxylic acidYield 11%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Procedure

To a solution of 1-benzooxazol-5-yl-cyclopropanecarboxylic acid methyl ester (2.9 g) in EtSH (30 mL) was added AlCl3 (5.3 g, 40 mmol) in portions at 0° C. The reaction mixture was stirred for 18 hours at room temperature. Water (20 mL) was added dropwise at 0° C. The resulting mixture was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 1:2) to give 1-(benzo[d]oxazol-5-yl)cyclopropanecarboxylic acid (280 mg, 11% over two steps). 1H NMR (DMSO, 400 MHz) δ12.25 (brs, 1H), 8.71 (s, 1H), 7.70-7.64 (m, 2H), 7.40 (dd, J=1.6, 8.4 Hz, 1H), 1.49-1.46 (m, 2H), 1.21-1.18 (m, 2H). MS (ESI) m/e (M+H+) 204.4.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated under vacuum
  4. customto give the crude product, which
  5. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-cc1700f00f464158aa3e1b41061d13ef
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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