Methyl acetoacetate → HCID 54721671, compound

HRID 481840Notes

Reaction equation

HRID 481840 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)C=O>CCCCCC.O1CCCC1>[Cl:16][C:17]1[CH:24]=[C:23]([CH:8]2[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)[CH:22]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 114773-ChlorobenzaldehydeHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 54721671HCID 54721671, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 1 using 5.0 mL of methyl acetoacetate, 2.0 g of NaH 60% dispersion in oil, 25 mL of 2.0M n-butyl lithium in hexane, 6.5 mL of 3-chlorobenzaldehyde and 150 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 15 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 122°-124° C.). 'H NMR (CDCl3) δ2.83 (dd, 1H), 2.96 (dd, 1H), 3.60 (dd, 2H), 5.68 (dd, 1H), 7.25-7.42 (m, 4H).

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-9d2caf249123429c8a65dad13cdd2e7c
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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