Acetate → HCID 22414832, compound

HRID 1721429Notes

Reaction equation

HRID 1721429 reaction equation
O=[O+][O-].C([O:7][C:8]1[C:16]([CH2:17][CH:18]=C)=[CH:15][C:14]([CH3:20])=[C:13]2[C:9]=1[C:10]([CH3:30])([CH3:29])[C:11](=[O:28])[N:12]2[CH2:21][C:22]1[CH:27]=CC=C[CH:23]=1)(=O)C.[CH3:31]SC.[C:34]([O-])(=[O:36])[CH3:35].C([O:41][CH2:42][CH3:43])(=O)C>>[CH2:17]([CH:16]([C:8]1[C:42]([OH:41])=[C:43]2[C:11](=[C:10]([CH3:30])[CH:9]=1)[NH:12][C:21](=[O:36])[C:22]2([CH3:27])[CH3:23])[CH:15]=[CH2:14])[CH3:18].[OH:7][C:8]1[C:16]([CH:34]([CH3:35])[CH:31]=[CH:42][CH3:43])=[CH:15][C:14]([CH3:20])=[C:13]2[C:9]=1[C:10]([CH3:29])([CH3:30])[C:11](=[O:28])[NH:12]2

Participants

7

Reactant 5

HCID 175AcetateHCID 1068Dimethyl SulfideHCID 8857Ethyl AcetateHCID 24823OzoneHCID 22414908HCID 22414908, compound

Product 2

HCID 22414832HCID 22414832, compoundHCID 54049941HCID 54049941, compound

Conditions

Temperature
50 °C

Procedure

Ozone was bubbled through a solution of 8.2 g (22.6 mmol) of 4-acetoxy-5-allyl-1-benzyl-2,3-dihydro-3,3,7-trimethyl-1H-indol-2-one in 2 l of ethyl acetate for 3 hours under cooling with ice. After bubbling nitrogen through the reaction mixture, 34.6 g (558 mmol) of dimethylsulfide was added and the mixture was stirred for one hour at 50° C. The solvent was evaporated and the residue was dissolved in 800 ml of methanol, followed by addition of 15.7 g (47 mmol) of methyltriphenylphosphoranilidene acetate. The mixture was stirred overnight. After evaporating the solvent from the reaction mixture, the residue was purified by column chromatography (silica gel, 3:1 mixture of n-hexane and ethyl acetate) to obtain 1.5 g (yield, 15.7%) of the title compound (a) and 480 mg (yield, 5.0%) of the title compound (b), each as a light yellow oil.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in 800 ml of methanol
  5. stirringThe mixture was stirred overnight
  6. customAfter evaporating the solvent from the reaction mixture
  7. customthe residue was purified by column chromatography (silica gel, 3:1 mixture of n-hexane and ethyl acetate)
  8. customto obtain

Sources & evidence

ORD record
ord-a3326608e01f4edbb1372890a9c506e3
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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