Citric Acid → HCID 7219635, compound

HRID 656254Notes

Reaction equation

[OH-].[K+].[C:3](O)(=O)[CH2:4][C:5]([CH2:10][C:11]([OH:13])=O)([C:7]([OH:9])=[O:8])O.[CH3:16]N(C)C=O>>[C@@H:4]12[O:13][C@@H:11]([CH:16]=[CH:3]1)[CH2:10][C@@H:5]2[C:7]([OH:9])=[O:8]

Participants

Reactant 3

HCID 311Citric Acid

HCID 6228Dimethylformamide

HCID 14797Potassium Hydroxide

Product 1

HCID 7219635HCID 7219635, compound

Conditions

Temperature: 60 °C

Procedure

A solution of 1 mmol of (1R,2R)-2-(naphthalene-2-sulphonyl)cyclohexyl ester (exo)-(1R,2S,4R)-7-oxabicyclo[2.2.1]-hept-5-ene-2-carboxylate in 5 ml of N,N-dimethylformamide is mixed with 2 mmol of potassium hydroxide and stirred at 60° C. for 17 hours. The reaction mixture is cooled to room temperature and, after addition of 1M citric acid solution, extracted with tert-butyl methyl ether (3×). The combined organic phases are washed with cold water and cold brine, dried with sodium sulphate and evaporated at room temperature. The title compound is identified by means of the Rf from the residue by flash chromatography (SiO2 60 F).

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionextracted with tert-butyl methyl ether (3×)
washThe combined organic phases are washed with cold water and cold brine
dry with materialdried with sodium sulphate
customevaporated at room temperature

Sources & evidence

ORD record: ord-76d18b15c8c64890912e8900e8f20340
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071651B2

Reaction notes

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