Hydrogen Bromide → HCID 10246918, compound

HRID 2086519Notes

Reaction equation

HRID 2086519 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][Si](C(C)(C)C)(C)C)=[CH:9][C:8]=1[CH2:21][CH:22]=[C:23]([CH2:27][CH2:28][CH:29]=[C:30]([CH3:37])[CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])[C:24]([OH:26])=[O:25])(C)(C)C.[F-].[K+].Br.Cl>CN(C=O)C>[CH3:35][C:34]([CH3:36])=[CH:33][CH2:32][CH2:31]/[C:30](/[CH3:37])=[CH:29]/[CH2:28][CH2:27]/[C:23](/[C:24]([OH:26])=[O:25])=[CH:22]/[CH2:21][C:8]1[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:7]=1[OH:6]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 69890146HCID 69890146, compound

Product 1

HCID 10246918HCID 10246918, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To cleave off the tert.-butyidimethylsilyl groups, 0,10 g of [2′-(2,5-bis[(tert.-butyldimethylsilyl)oxy]phenyl)ethylidene]-6,10-dimethyl-5,9-undecadienic acid is dissolved in 10 ml of DMF together with 2 equivalents of anhydrous potassium fluoride and 0.2 equivalents of 48% aqueous HBr, followed by stirring at room temperature for 24 hours under an argon atmosphere. Then, 10 ml of 2.0 M aqueous HCl solution is added, and the reaction mixture is extracted three times with 15 ml each of ether. The combined organic phases are washed with 10 ml of saturated aqueous NaCl solution, dried over MgSO4 and concentrated under reduced pressure. Purification of the raw product is effected by column chromatography (mobile system heptane:ethyl acetate=1:1). The yield was 87% of ganomycin B.

Workup

  1. extractionthe reaction mixture is extracted three times with 15 ml each of ether
  2. washThe combined organic phases are washed with 10 ml of saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the raw product

Sources & evidence

ORD record
ord-8c99df55400d48bc8ece0a836375a9ae
Source dataset
uspto-grants-2004_04
Patent number
US06726911B1

Reaction notes

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