Methyl acetoacetate → 5-Methyl-1-phenylhexan-1-one

HRID 481862Notes

Reaction equation

HRID 481862 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[C:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21].[Al+3].[Cl-].[Cl-].[Cl-]>CCCCCC.C1C=CC=CC=1.O1CCCC1>[OH:4][C:3]1[CH2:5][C:16]([CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:23][C:1](=[O:6])[CH:2]=1.[C:16]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

10

Reactant 5

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 5706925-Methyl-1-phenylhexan-1-oneHCID 6451240Aluminum(III) ChlorideHCID 178418339Butyllithium

Product 2

HCID 5706925-Methyl-1-phenylhexan-1-oneHCID 54703398HCID 54703398, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 14.2 mmol of methyl acetoacetate, 15.6 mmol of NaH 60% dispersion in oil, 14.9 mmol of 1.6M n-butyl lithium in hexane, 14.2 mmol of isoheptanophenone and 50 mL of tetrahydrofuran. Isoheptanophenone 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. 124°-125° C.). 1H NMR (CDCl3) δ0.80 (d,d, 6H), 1.1-1.2 (m, 2H), 1.15-1.40 (m, 2H), 1.4-1.5 (m, 1H), 1.9-2.0 (m, 2H), 2.88 (d, 1H), 2.9 (d, 1H), 3.2 (d, 1H), 3.3 (d, 1H), 7.2-7.5 (m, 5H).

Workup

  1. concentrationUpon concentrating
  2. customthe reaction
  3. customa solid precipitated out which
  4. customwas recrystallized from ethyl acetate (m.p. 124°-125° C.)

Sources & evidence

ORD record
ord-fb91f7de8e7645ae8852081de0504c26
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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