Sodium Iodide → HCID 126440, compound

HRID 1606335Notes

Reaction equation

HRID 1606335 reaction equation
C(OCCl)(=O)C(C)(C)C.[Na+].[CH2:11]([C:14]1[C:23]2[O:22][C:21]([C:24]([O-:26])=[O:25])=[CH:20][C:19](=[O:27])[C:18]=2[C:17]([O:28][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[CH:16][CH:15]=1)[CH:12]=[CH2:13].[I-].[Na+]>CC(C)=O>[CH2:11]([C:14]1[C:23]2[O:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][C:19](=[O:27])[C:18]=2[C:17]([O:28][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[CH:16][CH:15]=1)[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 87885Chloromethyl pivalateHCID 23669327Fpl 55618

Product 1

HCID 126440HCID 126440, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5.4 parts of chloromethyl pivalate in 60 parts of dry acetone were added 6 parts of 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid sodium salt and 0.1 parts of sodium iodide. The mixture was refluxed for 10 hours, cooled and evaporated to an oil which was dissolved in diethyl ether. The ethereal solution was filtered and evaporated under vacuum to give an oil which solidified when triturated with petroleum ether (b.p. 40°-60° C). The solid was filtered off and crystallised from petroleum ether (b.p. 60°-80° C) to give 4.5 parts of 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid pivaloyoxymethyl ester, m.p. 79°-80° C.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. temperaturecooled
  3. customevaporated to an oil which
  4. dissolutionwas dissolved in diethyl ether
  5. filtrationThe ethereal solution was filtered
  6. customevaporated under vacuum
  7. customto give an oil which
  8. customtriturated with petroleum ether (b.p. 40°-60° C)
  9. filtrationThe solid was filtered off
  10. customcrystallised from petroleum ether (b.p. 60°-80° C)

Sources & evidence

ORD record
ord-aaaa7709f8154e23a6b29e8d5568147f
Source dataset
uspto-grants-1976_04
Patent number
US03952104

Reaction notes

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