11-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one → HCID 19909555, compound

HRID 1534378Notes

Reaction equation

HRID 1534378 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.F[B-](F)(F)F.[O:33]=[N+:34]=[O:35]>C(Cl)Cl>[OH:8][C:6]1[C:5]2[O:9][C:10]3[CH:11]=[CH:12][C:13]([CH:22]([OH:27])[CH2:23][CH:24]([CH3:25])[CH3:26])=[C:14]([O:20][CH3:21])[C:15]=3[C:16](=[O:17])[O:18][CH2:19][C:4]=2[C:3]([N+:34]([O-:35])=[O:33])=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 12421311-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-oneHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 19909555HCID 19909555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-68 °C

Procedure

150 mg (0.4 mmol) of penicillide are dissolved in 15 ml of methylene chloride and stirred for 1 h under inert gas at a bath temperature of -68° C. after addition of 0.8 ml of a 0.5 molar solution of nitronium tetrafluoroborate. The reaction mixture is added to ice. After extraction with methylene chloride, washing with water and bicarbonate, drying and evaporating, the residue is chromatographed on silica gel in petroleum ether:ether=1:1. After evaporating, 86 mg (51% of theory) of yellowish solid are obtained.

Workup

  1. additionThe reaction mixture is added to ice
  2. extractionAfter extraction with methylene chloride
  3. washwashing with water and bicarbonate
  4. customdrying
  5. customevaporating
  6. customthe residue is chromatographed on silica gel in petroleum ether
  7. customAfter evaporating
  8. custom86 mg (51% of theory) of yellowish solid are obtained

Sources & evidence

ORD record
ord-6c7e4fb7c24c46e181d038c8c8e42a86
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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