Oxygen → HCID 9865002, compound

HRID 2399914Notes

Reaction equation

HRID 2399914 reaction equation
C[Si](C)(C)[C:3]1[O:7][C:6]([CH3:8])=[C:5]([CH2:9][O:10][C:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C(I)=C([OH:39])C(I)=C2OC3C(C4(OC(=O)C5C(Cl)=C(Cl)C(Cl)=C(Cl)C4=5)C=12)=CC(I)=C(O)C=3I.O=O.C(=O)=O.CC(C)=O>C1COCC1>[C:11]([O:10][CH2:9][C:5]1[CH:6]([CH3:8])[O:7][C:3](=[O:39])[C:4]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 977OxygenHCID 69439Rose Bengal LactoneHCID 18522661Acetone cardiceHCID 19385056HCID 19385056, compound

Product 1

HCID 9865002HCID 9865002, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of Compound 15 and Rose Bengal in THF was saturated with O2, then cooled to approximately -5° C. (dry ice/acetone bath) and irradiated with a 150 watt flood lamp (maintaining the temperature of the mixture at -5° to 0° C.) for 3 hours. The reaction mixture was then filtered and concentrated to a pink oil which was purified by column chromatography (eluent, EtOAc/hexanes, 1:20 to 1:4) to give 3.4 g (27%) of pure title compound as a colorless oil. An additional 3 g (approximately 25%) of a mixture of the title compound and the 5-desmethyl derivative (ratio 1:1 by proton NMR integration) was also obtained as a yellow oil.

Workup

  1. customirradiated with a 150 watt flood lamp (
  2. temperaturemaintaining the temperature of the mixture at -5° to 0° C.) for 3 hours
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated to a pink oil which
  5. customwas purified by column chromatography (eluent, EtOAc/hexanes, 1:20 to 1:4)

Sources & evidence

ORD record
ord-cee1577aa18446e994e10cc80d7ce36e
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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