Tetrahydrofuran → 6-Bromo-2-oxohexahydro-2H-3,5-methanocyclopenta[b]furan-7-carboxylic acid

HRID 1866592Notes

Reaction equation

HRID 1866592 reaction equation
[OH-:1].[Na+].[CH2:3]1[CH:7]2[C@H:8]3[C:13](=[O:14])[O:12][C:10](=[O:11])[C@H:9]3[CH:4]1[CH:5]=[CH:6]2.O1CCCC1.[Br:20]Br>O>[Br:20][CH:6]1[CH:5]2[CH:4]3[CH:9]([CH:8]([C:13]([OH:12])=[O:14])[CH:7]1[CH2:3]3)[C:10](=[O:11])[O:1]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24408BromineHCID 75977HCID 75977, compound

Product 1

HCID 2214986-Bromo-2-oxohexahydro-2H-3,5-methanocyclopenta[b]furan-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

In a 50-mL one neck round bottom flask, sodium hydroxide, Catalog No. 655104 from Aldrich Co. (0.33 g) was dissolved in water (37 mL). In the same flask, cis-endo-5-norbornene-2,3-dicarboxylic anhydride, Catalog No. 247634 from Aldrich Co. (2.54 g), and tetrahydrofuran (5 mL) were added. The flask was heated while stirring in a 45° C. water bath for five minutes to dissolve then cooled in an ice bath to 5° C. Bromine, Catalog No. 207888 from Aldrich Co. (2.55 g) was added dropwise to the flask. After stirring for 14 hours at room temperature, extract the product in ethyl acetate (100 mL) and dry with magnesium sulfate. The product, 2-bromo-5-oxo-4-oxatricyclo[4.2.1.03,7]nonane-9-carboxylic acid (3.86 g) was isolated by removing ethyl acetate by rotary evaporation.

Workup

  1. temperatureThe flask was heated
  2. dissolutionto dissolve
  3. temperaturethen cooled in an ice bath to 5° C
  4. addition(2.55 g) was added dropwise to the flask
  5. stirringAfter stirring for 14 hours at room temperature
  6. extractionextract the product in ethyl acetate (100 mL)
  7. dry with materialdry with magnesium sulfate

Sources & evidence

ORD record
ord-a6e5909eea4544d9ae6c3f3adcd90fd3
Source dataset
uspto-grants-2009_12
Patent number
US07629424B2

Reaction notes

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