Water → HCID 87260387, compound

HRID 2356229Notes

Reaction equation

HRID 2356229 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:53]=[CH:54][CH:55]=1)[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])([CH2:25][O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][OH:24])=[C:15]([Cl:52])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:53]=[CH:54][CH:55]=1)[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([NH:44][C:45]([O:47][C:48]([CH3:50])([CH3:49])[CH3:51])=[O:46])([CH2:25][O:26][Si:27]([C:40]([CH3:42])([CH3:43])[CH3:41])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:23]=[O:24])=[C:15]([Cl:52])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 67076967HCID 67076967, compound

Product 1

HCID 87260387HCID 87260387, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 191 (940 mg) was dissolved in DMF (10 mL). To this solution, pyridinium dichromate (800 mg) was added and the mixture was stirred for 48 hours at room temperature. Following addition of water, the mixture was extracted with ethyl acetate. The extract was then washed sequentially with water and a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate. The solvent was concentrated and the residue was purified on a silica gel chromatography (hexane:ethyl acetate=3:1) to give the desired product as a colorless oil (710 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was then washed sequentially with water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated
  5. customthe residue was purified on a silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e486df739706430bade4dc764dc46266
Source dataset
uspto-grants-2010_07
Patent number
US07759326B2

Reaction notes

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