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1,2-Dichloroethane → HCID 58355688, compound

HRID 1184218
Notes
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Reaction equation

HRID 1184218 reaction equation
[N+:1](=[C:3]([C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:4]([O:6][CH3:7])=[O:5])=[N-].[C:16]1([NH:22][C:23](N)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ClCCCl.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Rh+4]>[CH3:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]1[N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23](=[O:24])[NH:1][C:3]=1[C:4]([O:6][CH3:7])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6145PhenylureaHCID 6422Trifluoroacetic acidHCID 76731428Methyl 2-diazo-7-methoxy-3-oxoheptanoate

Product 1

HCID 58355688HCID 58355688, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 178476542
HCID 178476542, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-diazo-7-methoxy-3-oxoheptanoate (6.93 g) and 1-phenylurea (5.41 g) were suspended in toluene (30 ml)-1,2-dichloroethane (30 ml), rhodium tetraacetate (230 mg) was added and the mixture was stirred at 80° C. for 2 hr. After cooling to room temperature, trifluoroacetic acid (7.5 ml) was added and the reaction mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (15:85-100:0) was concentrated under reduced pressure to give the object product (7.40 g).

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature
  3. stirringthe reaction mixture was stirred at room temperature for 1 day
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (15:85-100:0)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-aaf21a8d65614f9ca2ee2b9a6acdc110
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08664380B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes