Sodium Acetate → HCID 54552778, compound

HRID 2232659Notes

Reaction equation

HRID 2232659 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[CH3:17][O:18][C:19]([C:21]1([CH:24]([OH:37])[CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[CH2:23][O:22]1)=[O:20].CCCCCC.C(OCC)C>C(Cl)Cl.C(OCC)C>[CH3:17][O:18][C:19]([C:21]1([C:24](=[O:37])[CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[CH2:23][O:22]1)=[O:20]

Participants

7

Reactant 4

HCID 517045Sodium AcetateHCID 21584099Diethylether hexaneHCID 53948093HCID 53948093, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 54552778HCID 54552778, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 9.05 g (42 mmol) of pyridinium chlorochromate and 3.4 g (42 mmol) of sodium acetate in 150 ml of methylene chloride is added 2.2 g (7 mmol) of 2-[5-(4-chlorophenoxy)-1-hydroxypentyl]-2-oxiranecarboxylic acid methyl ester of Example 2, part 2. The mixture is stirred for 4 hours, is diluted with ethyl ether and is filtered through Florisil. The solution is rotoevaporated and is chromatographed preparatively on silica gel using hexane:ethyl ether (3:2) as eluting solvent. The appropriate fractions are combined, washed with aqueous copper sulfate and brine and dried over magnesium sulfate. Filtration and rotoevaporation gives crude product. Column chromatography (silica gel; hexane:ethyl ether (3:2)) affords 523 mg (23.9%) of the title compound: IR (film) 1746, 1717 cm-1 ; NMR (CDCl3) δ 1.80 (4H, m), 2.66 (2H, m), 3.08 (1H, d, J=6 Hz), 3.34 (1H, d, J=6 Hz), 3.84 (3H, s), 3.94 (2H, t, J=6 Hz), 6.82 (2H, d, J=10 Hz) and 7.24 (2H, d, J=10 Hz).

Workup

  1. filtrationis filtered through Florisil
  2. customis chromatographed preparatively on silica gel
  3. washas eluting solvent
  4. washwashed with aqueous copper sulfate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and rotoevaporation
  7. customgives crude product

Sources & evidence

ORD record
ord-90c22c5df6ff464d9b750f5f032c95a3
Source dataset
uspto-grants-1988_11
Patent number
US04788306

Reaction notes

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