Water → HCID 69023608, compound

HRID 1866593Notes

Reaction equation

[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].[CH2:13]1[CH:17]2[C@H:18]3[C:23](=[O:24])[O:22][C:20](=[O:21])[C@H:19]3[CH:14]1[CH:15]=[CH:16]2.O>CC(C)=O.CN(C)C1C=CN=CC=1>[OH:6][C:5]1[C@@H:7]([C@@H:9]([OH:10])[CH2:11][O:12][C:23]([CH:18]2[CH:17]3[CH2:13][CH:14]([CH:15]=[CH:16]3)[CH:19]2[C:20]([OH:22])=[O:21])=[O:24])[O:8][C:2](=[O:1])[C:3]=1[OH:4]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 50-mL one neck round bottom flask, ascorbic acid, Catalog No. A92902 from Aldrich Co. (4.80 g) was dissolved in acetone (16.42 g). In the same flask, cis-endo-5-norbornene-2,3-dicarboxylic anhydride, Catalog No. 247634 from Aldrich Co. (4.42 g), and 4-dimethylaminopyridine, Catalog No. 522821 from Aldrich Co. (0.06 g), were added. The flask was heated while stirring in a 60° C. oil bath for 48 hours. Water (15 mL) was added and the flask was heated for another 12 hours. The product was extracted in ethyl acetate (100 mL) and dry with magnesium sulfate. The product, a mixture of bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid and 3-({(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethoxy}carbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid was isolated by removing ethyl acetate by rotary evaporation.

Workup

addition(0.06 g), were added
temperatureThe flask was heated
temperaturethe flask was heated for another 12 hours
extractionThe product was extracted in ethyl acetate (100 mL)
dry with materialdry with magnesium sulfate
additionThe product, a mixture of bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid

Sources & evidence

ORD record: ord-423dcf3268a6416ea7381895d5430707
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629424B2

Reaction notes

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