Water → HCID 15003164, compound

HRID 845554Notes

Reaction equation

HRID 845554 reaction equation
[CH2:1]([O:3][CH:4]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:26].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C=O)C>[CH2:1]([O:3][CH:4]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:5][CH2:6][CH2:7][CH2:8][C:9]([OH:26])=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 15003163HCID 15003163, compound

Product 1

HCID 15003164HCID 15003164, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.2 g of the product from example 22 in 15 ml of dry DMF was added in portions to a solution of pyridinium dichromate (4.4 g) in 30 ml of dry DMF. The solution was stirred at room temperature for 24 hours, then poured into water (300 ml). The aqueous mixture was extracted several times with Et2O, the combined extracts were washed with water and dried over Na2SO4. The reaction mixture was purified by column chromatography (SiO2) (1% MeOH/CHCl3). The partially purified product (0.54 g) was further purified by preparative thin layer chromatography (SiO2) (2% MeOH/CHCl3). Yield: 0.35 g.

Workup

  1. extractionThe aqueous mixture was extracted several times with Et2O
  2. washthe combined extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. customThe reaction mixture was purified by column chromatography (SiO2) (1% MeOH/CHCl3)
  5. customThe partially purified product (0.54 g) was further purified by preparative thin layer chromatography (SiO2) (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-c21be029cd46403bbc9070d988bb4045
Source dataset
uspto-grants-1988_07
Patent number
US04758594

Reaction notes

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