Potassium Carbonate → HCID 69966543, compound

HRID 1955809Notes

Reaction equation

HRID 1955809 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][CH3:17])=[CH:11][C:10]=2[N+:18]([O-])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.Cl[Sn]Cl.C([O-])([O-])=O.[K+].[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOC(C)=O.O.C(Cl)Cl.CCCCCC>[NH2:18][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH3:17])[CH:13]=[CH:14][C:9]=1[O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 61436Stannous chloride dihydrateHCID 69967781HCID 69967781, compound

Product 1

HCID 69966543HCID 69966543, compoundYield 32.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-[4-phenylmethoxy-3-nitrophenyl]propene (12.74 g, 47.3 mmol) and SnCl2.2H2O (53.4 g, 237 mmol) in 200 mL of EtOAc was refluxed for one hour. After cooling, 100 mL of hexane and then a solution of 41 g of K2CO3 (297 mmol) in 35 mL H2O were added with vigorous stirring, whereupon 300 mL of CH2Cl2 and 100 g Na2SO4 were added prior to filtration through Celite. After concentration, the residue was chromatographed twice on silica gel eluting with 7% to 17% Et2O/hexane to obtain 3.66 g of 1-[3-amino-4-phenylmethoxyphenyl]propene as a 98:2 mixture of trans to cis isomers. The title compound was prepared from 1-[3-amino-4-phenylmethoxyphenyl]propene following the procedure described in part 4 of step F of Example 1, except that the crude product was chromatographed on silica gel eluting with 50% EtOAc/hexane and then recrystallized from EtOAc/hexane to obtain 3.11 g.

Workup

  1. temperatureAfter cooling
  2. additionwere added
  3. filtrationto filtration through Celite
  4. concentrationAfter concentration
  5. customthe residue was chromatographed twice on silica gel eluting with 7% to 17% Et2O/hexane

Sources & evidence

ORD record
ord-bad56d69db454cf4a21993b9e56fbcfc
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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