Ethyl Acetoacetate → HCID 14010503, compound

HRID 2119198Notes

Reaction equation

HRID 2119198 reaction equation
[C:1]([O:7]CC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH3:10][Si:11](C(O)C)([CH3:13])[CH3:12]>C1(C)C=CC=CC=1>[C:1]([O:7][Si:11]([CH3:13])([CH3:12])[CH3:10])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 124478981-(Trimethylsilyl)ethanol

Product 1

HCID 14010503HCID 14010503, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl acetoacetate (2.60 g. 20 mmol; Aldrich) and trimethylsilylethanol (2.51 g, 21.1 mmol, Fluka) in toluene (100 ml) was heated and slowly distilled at 80°-100° with a Vigreaux column (1.7 cm×7 cm), removing most of the solvent over a period of 10 h. The residue was distilled under a reduced pressure with a Vigreaux column (1.7 cm×7 cm to obtain 3.34 g (16.5 mmol, yield 82.7%) of the title compound as a colourless oil: Rf 0.32 (20% ETOAc/Hex); bp 85°-88° C. (0.3 Torr); ir (neat) max : 1740 (ketone) and 1720 (ester) cm-1 ; 1Hmr (CDCl3) : 0.07 (9H, s, SiMe3), 1.00 (2H, `t` J=8 Hz, SiCH2), 1.93 (0.45H, s, MeC(OH)=), 2.28 (2.55H, s, MeCO), 3.12 (0.15H, s, OH of the enol form), 3.43 (1.7H, s, COCH2), 4.2 (2H, `t` J=8 Hz, CO2CH2), and 4.95 (0.15H, s, vinyl proton of the enol form) ppm;

Workup

  1. distillationslowly distilled at 80°-100° with a Vigreaux column (1.7 cm×7 cm)
  2. customremoving most of the solvent over a period of 10 h
  3. distillationThe residue was distilled under a reduced pressure with a Vigreaux column (1.7 cm×7 cm

Sources & evidence

ORD record
ord-c13e9f4f70434cf683618347cec227f2
Source dataset
uspto-grants-1987_07
Patent number
US04683296

Reaction notes

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