2-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate → HCID 59692641, compound

HRID 898846Notes

Reaction equation

HRID 898846 reaction equation
[C:1]([Si:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:6][CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:10])([CH3:4])([CH3:3])[CH3:2].[N+](=[C:31]([C:36]([O:38][CH3:39])=[O:37])[C:32]([O:34][CH3:35])=[O:33])=[N-]>C(Cl)(Cl)Cl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH3:35][O:34][C:32]([C:31]1([C:36]([O:38][CH3:39])=[O:37])[CH2:10][C:9]1([CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:33]

Participants

5

Reactant 2

HCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olateHCID 59692712HCID 59692712, compound

Product 1

HCID 59692641HCID 59692641, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of t-butyldiphenyl-(3-phenyl-3-butenyloxy)-silane (3.0 g, 7.0 mmol) and dimethyl diazomalonate (1.1 g, 7.0 mmol), which was synthesized by the method described in Synth. Commun. (1987, 17, 1709-1716), was added rhodium (II) acetate dimmer (62 mg, 0.14 mmol) under argon atmosphere, and the mixture was heated at 100° C. for 10 min. After cooling to room temperature, the mixture was diluted with chloroform (4 mL), separated and purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 4:1) to give the title compound (2.5 g, yield 70%) as a colorless oil.

Workup

  1. customwas synthesized by the method
  2. temperatureAfter cooling to room temperature
  3. customseparated
  4. custompurified by silica gel chromatography (hexane:ethyl acetate=100:0 to 4:1)

Sources & evidence

ORD record
ord-3058cbb5d76e4efaaf0a779e1457057b
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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