Methyl acetoacetate → 2-cyclopentyl-1-phenyl-ethanone

HRID 357829Notes

Reaction equation

HRID 357829 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH:16]1([CH2:21][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1.[Al+3].[Cl-].[Cl-].[Cl-]>CCCCCC.C1C=CC=CC=1.O1CCCC1>[CH:16]1([CH2:21][C:22]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:23][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)[CH2:20][CH2:19][CH2:18][CH2:17]1.[CH:16]1([CH2:21][C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

10

Reactant 5

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 6451240Aluminum(III) ChlorideHCID 122177442-cyclopentyl-1-phenyl-ethanoneHCID 178418339Butyllithium

Product 2

HCID 122177442-cyclopentyl-1-phenyl-ethanoneHCID 54690707HCID 54690707, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 25 mmol of methyl acetoacetate, 27.5 mmol of NaH 60% dispersion in oil, 26.25 mmol of 1.6M n-butyl lithium in hexane, 25 mmol of 2-cyclopentyl-1-phenyl-ethanone and 70 mL of tetrahydrofuran. 2-Cyclopentyl-1-phenyl-ethanone was prepared by reacting the appropriate acid chloride with AlCl3 in benzene as described by Vogel in Practical Organic Chemistry 1978, 770-775. Upon concentrating the reaction, a solid precipitated out which was recrystallized from ethyl acetate (m.p. 158°-160° C.). 1H NMR (DMSO-d6) δ 0.8-0.9 (m, 1 H), 1.0-1.1 (m, 1 H), 1.2-1.8 (m, 7 H), 1.9-2.1 (m, 2 H), 2.9 (ABq, 2 H), 4.8 (s, 1 H), 7.2-7.4 (m, 5 H), 11.3 (s, 1 H).

Workup

  1. concentrationUpon concentrating
  2. customthe reaction
  3. customa solid precipitated out which
  4. customwas recrystallized from ethyl acetate (m.p. 158°-160° C.)

Sources & evidence

ORD record
ord-846a2d426e404153a3deace76febfdb3
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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