Hydrogen Bromide → HCID 10246918、化合物

HRID 2086519ノート

反応式

HRID 2086519 の反応式
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]

参加物

6

反応物 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 69890146HCID 69890146、化合物

生成物 1

HCID 10246918HCID 10246918、化合物収率 87%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c99df55400d48bc8ece0a836375a9ae
出典データセット
uspto-grants-2004_04
特許番号
US06726911B1

反応ノート

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