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Magnesium → Ethyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-4-thiophenecarboxylate

HRID 1125
Notes
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Reaction equation

HRID 1125 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8](Br)=[CH:9]3)=[CH:4][C:3]1=2.[Mg].Br[C:22]1[S:23][CH:24]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:26]=1>C1COCC1.[Cl-].[Zn+2].[Cl-].Cl[Ni]Cl.CCN(CCOC1C=CC(CC2C=CC=CC=2)=CC=1)CC.Cl>[CH3:1][C:2]1([CH3:19])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([C:22]4[S:23][CH:24]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:26]=4)=[CH:9]3)=[CH:4][C:3]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 5462224MagnesiumHCID 152932155,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-bromoanthraceneHCID 15293216Ethyl 5-bromothiophene-3-carboxylate

Product 1

HCID 9821896Ethyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-4-thiophenecarboxylate

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalyst
HCID 86609808
NiCl2 dppe
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.5 g (30 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-bromoanthracene was added dropwise to a suspension of 724 mg (30 mmol) of magnesium in 10 ml of THF. Once the addition was completed, the mixture was heated at reflux for one hour. At room temperature 4.1 g (30 mmol) of anhydrous zinc chloride were added and the mixture was stirred for one hour. 5.2 g (22 mmol) of ethyl 2-bromo-4-thiophenecarboxylate and 120 mg (0.22 mmol) of the complex NiCl2 /DPPE were then added successively and the mixture was maintained under stirring at room temperature for 12 hours. The reaction medium was poured into ice-cold water, extracted with ethyl ether, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue obtained was chromatographed on a silica column eluted with a mixture of hexane and dichloromethane (60/40). After evaporation of the solvents, 6.35 g (74%) of the expected ester of melting point 107°-108° C. were recovered.

Workup

  1. additionOnce the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for one hour
  4. temperaturethe mixture was maintained
  5. stirringunder stirring at room temperature for 12 hours
  6. additionThe reaction medium was poured into ice-cold water
  7. extractionextracted with ethyl ether
  8. customthe organic phase decanted off
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. customThe residue obtained
  12. customwas chromatographed on a silica column
  13. washeluted with a mixture of hexane and dichloromethane (60/40)
  14. customAfter evaporation of the solvents, 6.35 g (74%) of the expected ester of melting point 107°-108° C.
  15. customwere recovered

Sources & evidence

ORD record
ord-5222a695140643c8a668e63555fad359
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723499

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes