HCID 57857051, compound → HCID 57857037, compound

HRID 561750Notes

Reaction equation

HRID 561750 reaction equation
[S:1]1[C:5]([C@H:6]([O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)/[CH:7]=[CH:8]/[C@H:9]2[C:13](=[CH2:14])[CH2:12][C@H:11]([OH:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][C:3]2[CH:43]=[CH:44][CH:45]=[CH:46][C:2]1=2.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.C(OCC)(=O)C>[S:1]1[C:5]([C@H:6]([O:25][Si:26]([C:39]([CH3:41])([CH3:42])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)/[CH:7]=[CH:8]/[C@H:9]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][C:3]2[CH:43]=[CH:44][CH:45]=[CH:46][C:2]1=2

Participants

5

Reactant 2

HCID 57857051HCID 57857051, compoundHCID 131709961Jones' reagent

Product 1

HCID 57857037HCID 57857037, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-25 °C

Procedure

(Z)-7-((1R,2R,5S)-2-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-5-hydroxy-3-methylenecyclopentyl)hept-5-enoic acid (23a) is dissolved in acetone (0.1 M) and cooled to −25° C. Jones reagent (1 molar equivalent) is added dropwise with stirring. Upon completion, as judged by TLC, the reaction is quenched with isopropyl alcohol and the crude reaction mixture is diluted with ethyl acetate, washed three times with brine, and dried over magnesium sulfate. After filtration and solvent evaporation, the product is purified by flash chromatography using hexanes-ethyl acetate as eluent to afford the title intermediate.

Workup

  1. customthe reaction is quenched with isopropyl alcohol
  2. customthe crude reaction mixture
  3. washwashed three times with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and solvent evaporation
  6. customthe product is purified by flash chromatography

Sources & evidence

ORD record
ord-0d167e761f8a4dbab18c12985e1b3a91
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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