Methanol → HCID 77230680, compound

HRID 2173140Notes

Reaction equation

HRID 2173140 reaction equation
CO.[CH3:3][C:4]1[C:13]([CH2:14][CH:15]=C)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][O:8][C:9]2=[O:17].[O:18]=[O+][O-].CSC>CCOC(C)=O>[CH3:3][C:4]1[C:13]([CH2:14][CH:15]=[O:18])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][O:8][C:9]2=[O:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 67515608HCID 67515608, compound

Product 1

HCID 77230680HCID 77230680, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a MeOH solution of 5-Methyl-6-(prop-2-en-1-yl)-3,4-dihydro-1H-isochromen-1-one (60 mg, 0.30 mmol) was bubbled ozone until it turned blue. Excess ozone was removed by bubbling nitrogen through. To the reaction was added DMS (0.22 ml, 3.0 mmol), and it was allowed to warm up slowly. The reaction was diluted with EtOAc, washed with water, and purified by MPLC to give the title compound. LC-MS (IE, m/z): 205 [M+1]+.

Workup

  1. customExcess ozone was removed
  2. customby bubbling nitrogen through
  3. temperatureto warm up slowly
  4. washwashed with water
  5. custompurified by MPLC

Sources & evidence

ORD record
ord-fd0e9a31496c4cc98e38c1c353e22fcf
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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