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Sigma-Aldrich

Ethyl 5-[(4-methylphenyl)sulfonyl]-3-oxopentanoate

95%

Synonym(s):

5-[(4-Methylphenyl)sulfonyl]-3-oxopentanoic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C14H18O5S
CAS Number:
1093348-62-9
Molecular Weight:
298.35
MDL number:
MFCD15144875
UNSPSC Code:
12352108
PubChem Substance ID:
329763568
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

42-46 °C

functional group

ester
ketone
sulfone

SMILES string

CCOC(=O)CC(=O)CCS(=O)(=O)c1ccc(C)cc1

InChI

1S/C14H18O5S/c1-3-19-14(16)10-12(15)8-9-20(17,18)13-6-4-11(2)5-7-13/h4-7H,3,8-10H2,1-2H3

InChI key

APRUPJUUTCSBAE-UHFFFAOYSA-N

Application

Ethyl 5-[(4-methylphenyl)sulfonyl]-3-oxopentanoate can be used as a reactant to prepare:
  • Ethyl 3-oxopent-4-enoate (Nazarov′s reagent) via base-induced β-elimination reaction.[1] Nazarov′s reagent can be employed as an anulating agent in Robinson annulation of cyclic β-diketones and cycloalkanones.[1]
  • γ-pyrones via triflic anhydride-mediated electrophilic condensation reaction.[2]

Reactant for:
  • Preparation of the Nazarov reagent via base-induced ß-elimination reaction

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

13 - Non Combustible Solids

WGK

nwg

Flash Point(F)

>230.0 °F - closed cup

Flash Point(C)

> 110 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKBC1505

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Direct synthesis of γ-pyrones by electrophilic condensation of β-ketoesters
Rodrigues CAB, et al.
Organic & Biomolecular Chemistry, 15(3), 680-683 (2017)
Ethyl 5-[(4-Methylphenyl) sulfonyl]-3-Oxopentanoate: A Bench-Stable Synthon for Ethyl 3-Oxopent-4-enoate (Nazarov?s Reagent)
Benetti S, et al.
Synlett, 2008(17), 2609-2612 (2008)

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