Ethylbenzene → HCID 18975701, compound

HRID 2393114Notes

Reaction equation

HRID 2393114 reaction equation
[CH:1]1([C:4]#[N:5])[CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].C(C1C=CC=CC=1)C.Cl[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1>CCCCCCC.O1CCCC1.CN1CCCN(C)C1=O>[CH:31]1([C:1]2([C:4]#[N:5])[CH2:3][CH2:2]2)[C:32]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][CH2:29][CH2:30]1

Participants

8

Reactant 4

HCID 7500EthylbenzeneHCID 79637CyclopropanecarbonitrileHCID 1887171-Chloro-1,2,3,4-tetrahydronaphthaleneHCID 2724682Lithium diisopropylamide

Product 1

HCID 18975701HCID 18975701, compoundYield 16.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8900HeptaneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

Cyclopropanecarbonitrile (17.14 g) was added dropwise to a mixture of lithium diisopropylamide solution (2M in a mixture of heptane, tetrahydrofuran and ethylbenzene; 128 ml), 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (30 ml) and tetrahydrofuran (240 ml) stirring at -78° C. under nitrogen. Stirring was continued for 1 hour at this temperature then a solution of 1-chlorotetralin (48.4 g) in tetrahydrofuran (50 ml) was added slowly and after a further hour the solution was allowed to warm to ambient temperature, then was heated under gentle reflux for 2 hours. The solvent was removed in vacuo and the residue acidified with concentrated hydrochloric acid then extracted with ethyl acetate (4×100 ml). The combined extracts were dried over magnesium sulphate and the solvent removed in vacuo to leave a semi-solid which was filtered and washed with acetonitrile, then recrystallised from acetone to give 1-(1,2,3,4-tetrahydronaphth-1-yl)cyclopropanecarbonitrile (8.3 g), mp 91°-93° C.

Workup

  1. temperaturewas heated
  2. temperatureunder gentle reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. extractionthen extracted with ethyl acetate (4×100 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulphate
  6. customthe solvent removed in vacuo
  7. customto leave a semi-solid which
  8. filtrationwas filtered
  9. washwashed with acetonitrile
  10. customrecrystallised from acetone

Sources & evidence

ORD record
ord-021d6befd68242f49c161307e2002e24
Source dataset
uspto-grants-1998_09
Patent number
US05804586

Reaction notes

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