Water → HCID 15003164, compound

HRID 478012Notes

Reaction equation

HRID 478012 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-e904a6f8f4594466a9391ae8d264d8aa
Source dataset
uspto-grants-1989_12
Patent number
US04889873

Reaction notes

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