Diazomethane → HCID 59364065, compound

HRID 1691531Notes

Reaction equation

HRID 1691531 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=3)[CH:15]=2)=[C:9]([CH3:34])[CH:8]=1)[CH3:2].[N+](=[CH2:37])=[N-].CN(N=O)C(N[N+]([O-])=O)=N.[OH-].[K+]>O1CCCC1.C(OCC)C.C(O)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH3:34])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH:28]4[CH2:37][CH:29]4[C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:27]=3)[CH:15]=2)=[C:11]([CH3:13])[CH:12]=1)[CH3:2]

Participants

9

Reactant 4

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 59364071HCID 59364071, compoundHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine

Product 1

HCID 59364065HCID 59364065, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (2E)-3-(4-{[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy}phenyl)acrylate (1.50 g, 3.26 mmol) in tetrahydrofuran (50 mL) was stirred under ice-cooling, and a solution of diazomethane prepared from N-methyl-N′-nitro-N-nitrosoguanidine (50% water-containing product, 4.98 g, 16.9 mmol) and 9.5 M aqueous potassium hydroxide solution (12.0 mL, 114 mmol) in diethyl ether (25 mL), and palladium(II) acetate (36.6 mg, 0.163 mmol) were alternately added thereto over 10 min in small portions. The reaction mixture was stirred for 5 hr, and acetic acid (3 drops) was added. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (1.53 g, yield 99%) as a colorless oil.

Workup

  1. temperaturecooling
  2. additionwere alternately added
  3. filtrationThe insoluble material was filtered off through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70)

Sources & evidence

ORD record
ord-cec8f32f7ad44e08bc06c16b8ceb5f9d
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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