Methyl acetoacetate → HCID 54687164, compound

HRID 1585392Notes

Reaction equation

HRID 1585392 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][CH2:20][CH2:21][CH3:22]>CCCCCC.O1CCCC1>[CH2:17]([C:16]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:23][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 74282HeptanophenoneHCID 178418339Butyllithium

Product 1

HCID 54687164HCID 54687164, 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 1.6 M n-butyl lithium in hexane, 25 mmol of heptanophenone and 70 mL of tetrahydrofuran. Upon concentrating the reaction, a solid precipitated out which was triturated with ether and filtered (m.p. 119-120.5° C.). 1H NMR (CDCl3) δ 0.84 (t, 3 H), 1.1-1.4 (m, 8 H), 1.9-2.0 (m, 2 H), 2.89 (d, 1 H), 2.93 (d, 1 H), 3.24 (d, 1 H), 3.35 (d, 1 H), 7.2-7.5 (m, 5 H).

Workup

  1. concentrationUpon concentrating
  2. customthe reaction
  3. customa solid precipitated out which
  4. customwas triturated with ether
  5. filtrationfiltered (m.p. 119-120.5° C.)

Sources & evidence

ORD record
ord-7e690c29898a4ddf8657131e991b6777
Source dataset
uspto-grants-1999_08
Patent number
US05936128

Reaction notes

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