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

HRID 1908362Notes

Reaction equation

HRID 1908362 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) δ 12.25 (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-7869583f7f934ce4b6d416b10d5fecee
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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