29780
Ethyl 2-oxocyclopentanecarboxylate
purum, ≥97.0% (GC)
Synonym(s):
2-(Ethoxycarbonyl)cyclopentanone, Ethyl cyclopentanone-2-carboxylate
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About This Item
Linear Formula:
(O=)C5H7CO2C2H5
CAS Number:
Molecular Weight:
156.18
EC Number:
210-253-0
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
387787
MDL number:
InChI key
JHZPNBKZPAWCJD-UHFFFAOYSA-N
InChI
1S/C8H12O3/c1-2-11-8(10)6-4-3-5-7(6)9/h6H,2-5H2,1H3
SMILES string
CCOC(=O)C1CCCC1=O
grade
purum
assay
≥97.0% (GC)
refractive index
n20/D 1.452 (lit.), n20/D 1.453
bp
102-104 °C/11 mmHg (lit.)
density
1.054 g/mL at 25 °C (lit.)
storage temp.
2-8°C
General description
Phase-transfer benzylation reaction of ethyl 2-oxocyclopentanecarboxylate with benzyl bromide has been investigated in microreactor. Ethyl 2-oxocyclopentanecarboxylate participates in cobalt(II) Schiff′s base complex catalyzed oxidation of primary and secondary alcohols to aldehydes and ketones.
Application
Ethyl 2-oxocyclopentanecarboxylate was used in stereoselective synthesis of (±)-cis,cis-spiro[4.4]nonane-1,6-diol. It was also used in synthesis of tanikolide.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
170.6 °F - closed cup
flash_point_c
77 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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A new synthesis of tanikolide.
Zhai H, et al.
Tetrahedron Letters, 44(14), 2893-2894 (2003)
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)
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