Isopropyl iodide → HCID 9866478, compound

HRID 1534366Notes

Reaction equation

HRID 1534366 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.[CH:28](I)([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:27][CH:22]([C:13]1[CH:12]=[CH:11][C:10]2[O:9][C:5]3[C:6]([O:8][CH:28]([CH3:30])[CH3:29])=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=3[CH2:19][O:18][C:16](=[O:17])[C:15]=2[C:14]=1[O:20][CH3:21])[CH2:23][CH:24]([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 12421311-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one

Product 1

HCID 9866478HCID 9866478, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg (0.54 mmol) of penicillide (Ib) in 2 ml of dimethylformamide are stirred under argon at 25° C. for 12 h with 0.5 ml (50 mmol) of isopropyl iodide and 160 mg (1.14 mmol) of anhydrous potassium carbonate. After evaporating in vacuo, the residue is taken up with 1 N aqueous hydrochloric acid and the mixture is exhaustively extracted with diethyl ether. After drying the organic phase, the evaporation residue is chromatographed on silica using petroleum ether/ether =1/1. Fractions which are pure by thin layer chromatography are combined and evaporated.

Workup

  1. customAfter evaporating in vacuo
  2. extractionthe mixture is exhaustively extracted with diethyl ether
  3. customAfter drying the organic phase
  4. customthe evaporation residue is chromatographed on silica
  5. customevaporated

Sources & evidence

ORD record
ord-b6ca38e062354a38a3047a538ae8071a
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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