[ CAS No. 21622-01-5 ] {[proInfo.proName]}

Name: 21622-01-5|Ethyl cyclopent-3-enecarboxylate|98%
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SKU: A221318
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Quality Control of [ 21622-01-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 21622-01-5 ]

CAS No. :	21622-01-5	MDL No. :	MFCD06410819
Formula :	C₈H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CTLAIKSGNQPPLO-UHFFFAOYSA-N
M.W :	140.18	Pubchem ID :	5314991
Synonyms :

Safety of [ 21622-01-5 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235	UN#:	3272
Hazard Statements:	H225	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 21622-01-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 21622-01-5 ]
Downstream synthetic route of [ 21622-01-5 ]

[ 21622-01-5 ] Synthesis Path-Upstream 1~1

1
[ 21622-01-5 ]
[ 25125-21-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With lithium aluminium tetrahydride; sodium hydroxide In tetrahydrofuran at -78℃; for 4 h; Inert atmosphere Stage #2: With sodium hydroxide In water at 0 - 20℃;	To a cold (—78° C.) solution of 703 (7 g, 50 mmol) in dry THF (150 mE) was added EiA1H4 (1 M soln in THF, 25 mE, 25 mmol), and the reaction solution was stirred at —78° C.under argon for 4 h. Then the reaction solution was allowed towarm to 0° C., and 2.5 mE of water, 2.5 mE of 15percent NaOH,and 7.5 mE of water were added sequentially. Afier warming to tt., the precipitates were filtered through a celite, and the celite was washed with hot EtOAc. The combined filtrateswere washed with 0.1 N NaOH, and brine, dried (MgSO4),filtered, concentrated and dried in vacuo to give 4.294 g(84percent) of 704 as a pale yellow liquid. ‘H NMR (400 MHz, CDC13) ö 5.68 (s, 2H, 2CH=CH), 3.57 (d, J=6.0 Hz, 2H, CH2OH), 2.54-2.48 (m, 3H, CH+CH2), 2.15-2.10 (m, 2H, CH2).

Reference： [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 5, p. 859 - 867
[2] Patent: US9180138, 2015, B2, . Location in patent: Page/Page column 58
[3] Patent: EP468119, 1992, A1,

[ 21622-01-5 ] Synthesis Path-Downstream 1~86

1
[ 18325-74-1 ]
[ 21622-01-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With 2,6-dibromophenol; tetraethyllead(IV); tungsten dioxydichloride; In toluene; at 90℃; for 1.5h;Inert atmosphere;	A flame-dried 500 mE flask was charged with 2,6-dibro- mophenol (1.20 g, 4.76 mmol), tungsten oxychloride (0.8 13 g, 2.38 mmol), and anhydrous toluene (25 mE). The resulting suspension was heated at reflux under nitrogen for 1 h, and then the solvent was evaporated in vacuo. The solid residue was broken up with a spatula and dried in vacuo for 30 mm. To the residue were added toluene (160 mE), Et4Pb (1.54 g, 4.76 mE), and 702 (22 g, 131.0 mmol). The mixture was heated at 90 C. under nitrogen for 1.5 h. After being cooled to r.t., the mixture was filtered through a celite, and the celite was rinsed with t-l3uOMe. The combined filtrates were washed with 1% NaOH soln, water, and brine, and concentrated by evaporation at reduced pressure. The residue was distilled (37-38 C/i Torr) to give 13.06 g (7 1%) of 703 as a colorless liquid.‘H NMR (400 MHz, CDC13) ö 5.67 (s, 2H, CHrrrCH), 4.14 (q, 2H, J=7.2 Hz, OCH2), 3.11 (pentuplet, J=7.6 Hz, 1H, CH),2.65 (d, J=7.6 Hz, 4H, 2CH2), 1.27 (t, J=7.2 Hz, 3H, CH3).

Reference： [1]Russian Chemical Bulletin,1994,vol. 43,p. 1425 - 1426
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation),1994,p. 1503 - 1504
[2]Journal of Organic Chemistry,1996,vol. 61,p. 7963 - 7966
[3]Journal of the American Chemical Society,1995,vol. 117,p. 8992 - 8998
[4]Patent: US9180138,2015,B2 .Location in patent: Page/Page column 57; 58
[5]Organometallics,2020,vol. 39,p. 3453 - 3457

2
[ 21622-01-5 ]
[ 115973-49-4 ]

Reference： [1]Synthetic Communications,1995,vol. 25,p. 3589 - 3595

3
[ 21622-00-4 ]
[ 21622-01-5 ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 8992 - 8998

4
[ 21622-01-5 ]
[ 183065-60-3 ]
cis-3,4-epoxycyclopentanecarboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7963 - 7966
[2]Journal of Organic Chemistry,1996,vol. 61,p. 7963 - 7966
[3]Organic process research and development,2020,vol. 24,p. 1294 - 1303

5
[ 21622-01-5 ]
[ 25125-21-7 ]

Yield	Reaction Conditions	Operation in experiment
84%		To a cold (-78 C.) solution of 703 (7 g, 50 mmol) in dry THF (150 mE) was added EiA1H4 (1 M soln in THF, 25 mE, 25 mmol), and the reaction solution was stirred at -78 C.under argon for 4 h. Then the reaction solution was allowed towarm to 0 C., and 2.5 mE of water, 2.5 mE of 15% NaOH,and 7.5 mE of water were added sequentially. Afier warming to tt., the precipitates were filtered through a celite, and the celite was washed with hot EtOAc. The combined filtrateswere washed with 0.1 N NaOH, and brine, dried (MgSO4),filtered, concentrated and dried in vacuo to give 4.294 g(84%) of 704 as a pale yellow liquid. ?H NMR (400 MHz, CDC13) oe 5.68 (s, 2H, 2CH=CH), 3.57 (d, J=6.0 Hz, 2H, CH2OH), 2.54-2.48 (m, 3H, CH+CH2), 2.15-2.10 (m, 2H, CH2).
	With sodium hydroxide; In water;	Step A : Preparation of 3-cyclopentenylmethanol 0.78 mol (109.45 g) of 3-cyclopentenylcarboxylic acid ethyl ester dissolved in 400 ml of anhydrous ether are added dropwise to a stirred suspension of 24 g of lithium aluminum hydride (0.7 mmol) in 500 ml of anhydrous ether. The reaction mixture is stirred at 20C for 3 hours and hydrolized by careful addition of 24 ml of water, 24 ml of 15% aqueous sodium hydroxide and three times 24 ml of water. The white precipitate is discarded by filtration and the filtrate is washed twice with brine, dried over sodium sulfate, filtered and evaporated to give 67.5 g of the product 3-cyclopentenylmethanol (88% yield) which is used in the next step without further purification.

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 859 - 867
[2]Patent: US9180138,2015,B2 .Location in patent: Page/Page column 58
[3]Patent: EP468119,1992,A1

8
[ 3195-24-2 ]
[ 21622-01-5 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7963 - 7966
[2]Journal of the American Chemical Society,1995,vol. 117,p. 8992 - 8998
[3]Journal of the American Chemical Society,1995,vol. 117,p. 8992 - 8998
[4]Advanced Synthesis and Catalysis,2011,vol. 353,p. 2363 - 2367
[5]Patent: US9180138,2015,B2

9
[ 21622-01-5 ]
[ 72656-82-7 ]