4-Chlorobenzaldehyde → HCID 54721559, compound

HRID 357806Notes

Reaction equation

HRID 357806 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][C:20](C=O)=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:8]2[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 54721559HCID 54721559, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 10 mL of methyl acetoacetate, 3.9 g of NaH 60% dispersion in oil, 58 mL of 1.6M n-butyl lithium in hexane, 13.5 g of 4-chlorobenzaldehyde and 250 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 15 minutes at 0°0 C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 149°-150° C.). 1H NMR (CDCl3) δ 2.83 (dd, 1 H), 2.95 (dd, 1 H), 3.60 (dd, 2 H), 5.67 (dd, 1 H), 7.33-7.44 (m, 4 H).

Workup

  1. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-7c53a3acd47b491aba57b96ed3208f52
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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