Diethyl Ether → HCID 15703807, compound

HRID 1534368Notes

Reaction equation

HRID 1534368 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]2[O:9][C:10]3[C:15]([C:16]([O:18][CH2:19][C:4]=2[CH:3]=1)=[O:17])=[C:14]([O:20][CH3:21])[C:13]([C@@H:22]([OH:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:12][CH:11]=3.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[OH:8][C:6]1[C:5]2[O:9][C:10]3[CH:11]=[CH:12][C:13]([C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[C:14]([O:20][CH3:21])[C:15]=3[C:16](=[O:17])[O:18][CH2:19][C:4]=2[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12421311-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 15703807HCID 15703807, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

800 mg (2.2 mmol) of penicillide (Ib) are stirred at 25° C. under argon for 3 h in 15 ml of methylene chloride and 880 mg (4.1 mmol) of pyridinium chlorochromate. After addition of 200 ml of diethyl ether, the mixture is filtered through silica gel Si60. The evaporation residue of the filtrate is chromatographed on silica gel using petroleum ether/ether =1:1

Workup

  1. filtrationthe mixture is filtered through silica gel Si60
  2. customThe evaporation residue of the filtrate is chromatographed on silica gel

Sources & evidence

ORD record
ord-951549fc39c4406fba8d57ebfa249297
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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