2-Chlorobenzaldehyde → HCID 54721677, compound

HRID 481849Notes

Reaction equation

HRID 481849 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:24]=[CH:23][CH:22]=[CH:21][C:18]=1C=O>CCCCCC.O1CCCC1>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:8]1[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]1

Participants

7

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 54721677HCID 54721677, 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 2.5 mL of methyl acetoacetate, 1.0 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 3.3 mL of 2-chlorobenzaldehyde and 75 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 10 minutes at 0° C. then stirred for 2 hours at room temperature. The crude product was triturated from diethyl ether to afford a solid (m.p. 124°-125° C.). 1H NMR (CDCl3) δ2.63 (dd, 1H), 3.10 (dd, 1H), 3.68 (dd, 2H), 6.07 (dd, 1H), 7.3-7.65 (m, 4H).

Workup

  1. stirringthen stirred for 2 hours at room temperature
  2. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-094f365dfdb040a1a5a5cbbb33b7d937
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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