Methyl acetoacetate → HCID 21222433, compound

HRID 481853Notes

Reaction equation

HRID 481853 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[H-].[Na+].C([Li])CCC.[C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]>CCCCCC.O1CCCC1>[CH3:20][CH:19]([CH3:21])[CH2:18][CH2:17][C:16]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:22][C:1](=[O:6])[CH:2]=[CH:3][CH2:5]1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 803014-Methyl-1-phenylpentan-1-oneHCID 178418339Butyllithium

Product 1

HCID 21222433HCID 21222433, compound

Reagents, catalysts & solvents 2

HCID 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 isohexanophenone and 70 mL of tetrahydrofuran. Upon concentrating the reaction a solid precipitated out which was triturated with ether and filtered (m.p. 134°-136° C.). 1H NMR (CDCl3) δ0.83 (dd, 6H), 1.1-1.3 (m, 2H), 1.4-1.6 (m, 1H), 1.9-2.1 (m, 2H), 2.90 (d, 1H), 2.92 (d, 1H), 3.25 (d, 1H), 3.35 (d, 1H), 7.2-7.5 (m, 5H).

Workup

  1. concentrationUpon concentrating
  2. customthe reaction a solid
  3. customprecipitated out which
  4. customwas triturated with ether
  5. filtrationfiltered (m.p. 134°-136° C.)

Sources & evidence

ORD record
ord-e9e0ce99a93a4bb1bfca27494299bb51
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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