1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide → HCID 86613309, compound

HRID 2378050Notes

Reaction equation

HRID 2378050 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3([CH2:25][OH:26])[CH2:24][CH2:23]3)[O:13][N:12]=2)=[CH:7][CH:6]=1.OI1(=O)C2C=CC=CC=2C(=O)O1>ClCCl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([C:22]3([CH:25]=[O:26])[CH2:23][CH2:24]3)[O:13][N:12]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 3394961-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxideHCID 68956272HCID 68956272, compound

Product 1

HCID 86613309HCID 86613309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture consisting of the substrate {1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropyl}-methanol (Examples 4-13 General Procedures, Coupling Method C, Step iii, 0.500 g) in dichloromethane (8 mL) is added 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (1.19 g.) The stirring mixture is brought to reflux till the substrate is not detected by methods such as thin layer chromatography or mass spectrometry. The mixture is then cooled to room temperature and filtered. The filtrate is concentrated under reduced pressure to afford the solid 1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarbaldehyde.

Workup

  1. temperatureto reflux till the substrate
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-6e2bf72cd7ef4976a84a0408f81b87bf
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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