Sodium Acetate → HCID 53733530, compound

HRID 2107130Notes

Reaction equation

HRID 2107130 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:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH2:23][O:22]1)=[O:20]>C(Cl)Cl.C(OCC)C>[CH3:17][O:18][C:19]([C:21]1([C:24](=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH2:23][O:22]1)=[O:20]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 53895241HCID 53895241, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 53733530HCID 53733530, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 11.6 g (54 mmol) of pyridinium chlorochromate and 4.4 g (54 mmol) of sodium acetate in 200 ml of methylene chloride is added 2.95 g (9 mmol) of 2-[6-(4-chlorophenoxy)-1-hydroxyhexyl]-2-oxiranecarboxylic acid methyl ester (isomer A) prepared according to the procedure of Example 2, part 2, at room temperature under a nitrogen atmosphere. The mixture is stirred for 4 hours, is diluted with 600 ml of ethyl ether and is filtered through Florisil. Rotoevaporation gives 2.2 g of crude product. Preparative column chromatography (silica gel:ethyl ether (3:2)) affords 1.66 g (56.4%) of the title compound: IR (film) 1746, 1719 cm-1 ; NMR (CDCl3) δ 1.49 (2H, p, J=8 Hz), 1.62-1.86 (4H, mc), 2.62 (2H, m), 3.05 (1H, d, J=6 Hz), 3.36 (1H, d, J=6 Hz), 3.86 (3H, s) 3.94 (2H, t, J=6 Hz), 6.84 (2H, d, J=8 Hz) and 7.27 (2H, d, J=8 Hz).

Workup

  1. customprepared
  2. customaccording to the procedure of Example 2, part 2, at room temperature under a nitrogen atmosphere
  3. filtrationis filtered through Florisil
  4. customRotoevaporation gives 2.2 g of crude product

Sources & evidence

ORD record
ord-6ac6838e41b7485b81c669ee0f51d946
Source dataset
uspto-grants-1990_06
Patent number
US04933365

Reaction notes

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