2-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate → HCID 59255985, compound

HRID 639855Notes

Reaction equation

HRID 639855 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[CH2:9])(=[O:4])=[O:3].[N+](=[C:20]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])=[N-]>ClC1C=CC=CC=1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[Cl:17][C:12]1[CH:11]=[C:10]([C:8]2([CH2:7][CH2:6][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:9][C:20]2([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

6

Reactant 2

HCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olateHCID 59255980HCID 59255980, compound

Product 1

HCID 59255985HCID 59255985, compound

Reagents, catalysts & solvents 3

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent2×

Procedure

In a round-bottomed flask, 3-(3,4-dichlorophenyl)-3-buten-1-yl methanesulfonate (P62, 90.8 g, 308 mmol) was dissolved in chlorobenzene (200 ml) to give a green solution. Rhodium acetate dimer (6.80 g, 15.38 mmol) was added. The suspension was warmed to an internal temperature of +65° C. and dimethyl diazopropanedioate (78 g, 492 mmol, for a reference procedure of preparation see Synthetic Communication 1987, 17 (14), 1709-1716) dissolved in chlorobenzene (150 ml) was added dropwise (during 2.5 hrs), keeping the internal temperature below 65-67° C. At the end of the addition, the mixture was cooled to room temperature. It was diluted with DCM (300 ml) and filtered over a celite pad to separate the catalyst.

Workup

  1. customto give a green solution
  2. customfor a reference procedure of preparation
  3. additionwas added dropwise (during 2.5 hrs)
  4. customthe internal temperature below 65-67° C
  5. additionAt the end of the addition
  6. filtrationfiltered over a celite pad
  7. customto separate the catalyst

Sources & evidence

ORD record
ord-af9f21e2b490457490c5d292bb3706fb
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

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