Water → HCID 59129328, compound

HRID 1403871Notes

Reaction equation

HRID 1403871 reaction equation
C(O/[N:5]=[C:6](/[C:8]1[CH:9]=[C:10]([C:15]2([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16]2)[CH:11]=[CH:12][C:13]=1[OH:14])\[CH3:7])(=O)C.N1C=CC=CC=1.O>CN(C=O)C>[CH3:7][C:6]1[C:8]2[CH:9]=[C:10]([C:15]3([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16]3)[CH:11]=[CH:12][C:13]=2[O:14][N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 136341639HCID 136341639, compound

Product 1

HCID 59129328HCID 59129328, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (E)-methyl 1-(3-(1-(acetoxyimino)ethyl)-4-hydroxyphenyl)cyclopropane carboxylate (10.5 g, 39.6 mmol) and pyridine (31.3 g, 396 mmol) in DMF (150 mL) was heated at 125° C. for 10 h. The cooled reaction mixture was poured into water (250 mL) and 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 50:1) to give methyl 1-(3-methylbenzo[d]isoxazol-5-yl)cyclopropanecarboxylate (7.5 g, 82%). 1H NMR (CDCl3 300 MHz) δ 7.58-7.54 (m, 2H), 7.48 (dd, J=1.5, 8.1 Hz, 1H), 3.63 (s, 3H), 2.58 (s, 3H), 1.71-1.68 (m, 2H), 1.27-1.23 (m, 2H).

Workup

  1. customThe cooled reaction mixture
  2. extractionwas extracted with EtOAc (100 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. customto give the crude product, which
  6. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-91906470c24045ceb93607f8e9e5ea62
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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