Hydrochloric Acid → 6-Fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid

HRID 2417313Notes

Reaction equation

HRID 2417313 reaction equation
[OH-].[Na+].[F:3][C:4]1([C:11]([O:13]CC)=[O:12])[CH:9]2[CH:5]1[CH2:6][CH2:7][C:8]2=[O:10].Cl>>[F:3][C:4]1([C:11]([OH:13])=[O:12])[CH:9]2[CH:5]1[CH2:6][CH2:7][C:8]2=[O:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9964278Ethyl(1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate

Product 1

HCID 226347796-Fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylic acidYield 103.9%

Procedure

A 1M aqueous solution of sodium hydroxide in an amount of 1.0 mL was added dropwise to 0.17 g of (1RS,5RS,6RS)ethyl 6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate while being ice-cooled. The mixture was stirred for 2.5 hours at the same temperature. The pH of the reaction mixture was adjusted to 1 with concentrated hydrochloric acid, followed by extractions with chloroform three times. The organic layers were combined, and the combined organic layer was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure, thereby yielding 0.15 g of (1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid.

Workup

  1. temperaturecooled
  2. extractionfollowed by extractions with chloroform three times
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb26b8d515374bccafffc0dcd1248518
Source dataset
uspto-grants-2004_11
Patent number
US06825375B2

Reaction notes

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