168092

Sigma-Aldrich

Ethyl 2-oxocyclopentanecarboxylate

95%

Synonym(s):
Ethyl cyclopentanone-2-carboxylate, 2-(Ethoxycarbonyl)cyclopentanone
Linear Formula:
(O=)C5H7CO2C2H5
CAS Number:
Molecular Weight:
156.18
Beilstein/REAXYS Number:
387787
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

95%

refractive index

n20/D 1.452 (lit.)

bp

102-104 °C/11 mmHg (lit.)

density

1.054 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C1CCCC1=O

InChI

1S/C8H12O3/c1-2-11-8(10)6-4-3-5-7(6)9/h6H,2-5H2,1H3

InChI key

JHZPNBKZPAWCJD-UHFFFAOYSA-N

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General description

Phase-transfer benzylation reaction of ethyl 2-oxocyclopentanecarboxylate with benzyl bromide in microreactor has been investigated. Ethyl 2-oxocyclopentanecarboxylate participates in cobalt (II) Schiff′s base complex catalyzed oxidation of primary and secondary alcohols.

Application

Ethyl 2-oxocyclopentanecarboxylate was used in stereoselective synthesis of (±)-cis,cis-spiro4.4nonane-1,6-diol. It was also used in the synthesis of tanikolide.

Packaging

25, 100 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

170.6 °F - closed cup

Flash Point(C)

77 °C - closed cup

Masaharu Ueno et al.
Chemical communications (Cambridge, England), (8)(8), 936-937 (2003-05-15)
Phase-transfer alkylation in a microreactor proceeds smoothly, and the reaction has been found to be more efficient than that in a round-bottomed flask with vigorous stirring; we have observed by an optical microscope study that an interfacial area provided by...
An improved synthesis and resolution of (?)-< i> cis, cis</i>-spiro [4.4] nonane-1, 6-diol.
Nieman JA, et al.
Tetrahedron Asymmetry, 4(9), 1973-1976 (1993)
Cobalt (II) Schiff's base complex catalysed oxidation of alcohols with dioxygen in the presence of ethyl 2-oxocyclopentanecarboxylate.
Punniyamurthy T and Iqbal J.
Tetrahedron Letters, 35(23), 4007-4010 (1994)
A new synthesis of tanikolide.
Zhai H, et al.
Tetrahedron Letters, 44(14), 2893-2894 (2003)

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