HCID 45120113, compound → HCID 66602031, compound

HRID 1255400Notes

Reaction equation

HRID 1255400 reaction equation
Cl[CH:2]1[C:8](=[O:9])[CH:7]2[O:10][CH:4]([CH:5]=[CH:6]2)[C:3]1=[O:11]>Cl.[Zn]>[CH:7]12[O:10][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:11])[CH2:2][C:8]2=[O:9]

Participants

4

Reactant 1

HCID 45120113HCID 45120113, compound

Product 1

HCID 66602031HCID 66602031, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolvent

Procedure

To a stirred suspension of 3-chloro-8-oxa-bicyclo[3.2.1]oct-6-ene-2,4-dione (6.44 g) in aqueous hydrochloric acid (35 ml, 2M) was added zinc powder (4.88 g) in portions maintaining the reaction temperature below 25° C. by cooling with an icebath. After 45 minutes, the mixture was filtered through a bed of celite then extracted with ethyl acetate. the extract was dried over magnesium sulfate, filtered and evaporated under reduced pressure to afford the required product. 1H NMR (d6-DMSO) δ: 6.50 (2H, s), 5.18 (2H, s), 4.15 (1H, d), 3.34 (1H, d).

Workup

  1. temperaturemaintaining the reaction temperature below 25° C.
  2. temperatureby cooling with an icebath
  3. filtrationthe mixture was filtered through a bed of celite
  4. extractionthen extracted with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1bc2af3138b644f5941fcc353595cab3
Source dataset
uspto-grants-2013_06
Patent number
US08461083B2

Reaction notes

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