Water → HCID 18786647, compound

HRID 1108054Notes

Reaction equation

HRID 1108054 reaction equation
CN(C)[C:3]1[CH2:10][CH2:9][C:8]2[C:4]=1[CH:5]=[CH:6][CH:7]=2.[CH:12]1([Li])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.O>O1CCCC1>[CH:12]1([C:3]2[CH2:10][CH2:9][C:8]3[C:4]=2[CH:5]=[CH:6][CH:7]=3)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 13280604HCID 13280604, compoundHCID 178506815HCID 178506815, compound

Product 1

HCID 18786647HCID 18786647, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 12.5 g (85 mmol) of 4-(dimethylamino)-5,6-dihydropentalene in 50 ml of tetrahydrofuran are admixed with a solution of 10.4 g (85 mmol) of indenyllithium in 20 ml of tetrahydrofuran. The reaction solution is stirred for 24 hours at room temperature and the reaction is stopped by addition of water. Extraction with diethyl ether, drying of the organic phases over MgSO4 and removal of the solvent under reduced pressure and subsequent recrystallization of the crude product from diethyl ether gives 13.9 g (75%) of 4-indenyl-5,6-dihydropentalene.

Workup

  1. extractionExtraction with diethyl ether
  2. dry with materialdrying of the organic phases over MgSO4 and removal of the solvent under reduced pressure and subsequent recrystallization of the crude product from diethyl ether

Sources & evidence

ORD record
ord-e69946b41131488c8ea0e9c6c1ac5cf4
Source dataset
uspto-grants-2000_05
Patent number
US06063949

Reaction notes

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