Diethyl Ether → HCID 18516692, compound

HRID 1369902Notes

Reaction equation

HRID 1369902 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)=[C:11]([CH3:12])[C:6]=2[O:5][C:4](=[O:19])[CH:3]=1.[C:20]1([C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N+]=[N-])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOCC>CN(C=O)C>[C:20]1([CH:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[O:1][C:2]2[C:7]3[CH:8]=[CH:9][C:10]([CH:13]4[CH2:18][CH2:17][CH2:16][CH2:15][O:14]4)=[C:11]([CH3:12])[C:6]=3[O:5][C:4](=[O:19])[CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 612301,1'-(Diazomethylene)bis(benzene)2×HCID 57234141HCID 57234141, compound

Product 1

HCID 18516692HCID 18516692, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

55 g of 4-hydroxy-8-methyl-7-(tetrahydro-2H-pyran-2-yl)-2H-1-benzopyran-2-one is introduced into 250 ml of anhydrous dimethylformamide heated to 40° C., and a solution of 58.3 g of diphenyldiazomethane in 250 ml of DMF is added dropwise. The addition is made over 3 hours while maintaining the temperature at 40° C. Several portions of 3 g of diphenyldiazomethane are added again and agitation is carried out for one hour at 40° C. The reaction medium is poured into 2 l of sulphuric ether. The organic solution is washed with an aqueous solution of sodium bicarbonate, with a solution of soda (0.1 M), with water and with salt water followed by evaporation to dryness. The residue is agitated in an isopropyl ether-hexane mixture (1-2) followed by separation. The insoluble part is dried. 20.5 g of sought product is obtained.

Workup

  1. additionThe addition
  2. temperaturewhile maintaining the temperature at 40° C
  3. waitagitation is carried out for one hour at 40° C
  4. washThe organic solution is washed with an aqueous solution of sodium bicarbonate, with a solution of soda (0.1 M), with water and with salt water
  5. customfollowed by evaporation to dryness
  6. customfollowed by separation
  7. customThe insoluble part is dried

Sources & evidence

ORD record
ord-e7640aaed784442ab4aff0e2aac8e699
Source dataset
uspto-grants-2003_06
Patent number
US06579902B1

Reaction notes

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