1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22267232, compound

HRID 488876Notes

Reaction equation

HRID 488876 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[CH2:16][O:17]C(=O)C)[O:12][C:11](=[O:21])[C:10]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:9]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)C.C1CCN2C(=NCCC2)CC1>C(O)C.C(OCC)(=O)C>[OH:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[CH2:16][OH:17])[O:12][C:11](=[O:21])[C:10]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:9]2[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22267291HCID 22267291, compound

Product 1

HCID 22267232HCID 22267232, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-[6,7-bis(acetoxymethyl)-2-oxo-4-phenyl-2H-chromen-3-yl]acetate (240 mg) in ethanol (4 ml) was combined with DBU (0.4 ml), and stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate (30 ml), and then washed with a 1 N solution of hydrochloric acid followed by a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and after drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The resultant residue was recrystallized from ether to obtain the title compound (167 mg, yield: 86%). Melting point: 130-131° C.

Workup

  1. washwashed with a 1 N solution of hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and after drying over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resultant residue was recrystallized from ether

Sources & evidence

ORD record
ord-f59a5f4111e54e67b35548df560d0e09
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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