40915-37-5|3,4-Dihydro-2H-pyran-5-carboxylic acid| Ambeed

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Quality Control of [ 40915-37-5 ] Purity: 98% SDS Specification

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Product Details of [ 40915-37-5 ]

CAS No. :	40915-37-5
Formula :	C₆H₈O₃
M.W :	128.13
SMILES Code :	O=C(C1=COCCC1)O
MDL No. :	MFCD06203171
InChI Key :	MIBCYYGVLHFYSD-UHFFFAOYSA-N
Pubchem ID :	13705403

Safety of [ 40915-37-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P301+P312+P330

Application In Synthesis of [ 40915-37-5 ]

* 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.

Downstream synthetic route of [ 40915-37-5 ]

[ 40915-37-5 ] Synthesis Path-Downstream 1~35

1
[ 110-87-2 ]
[ 40915-37-5 ]

References: [1]Synthesis,1986,p. 1016 - 1017.
[2]Synthesis,1986,p. 1016 - 1017.
[3]Marine Drugs,2013,vol. 11,p. 5159 - 5189.
[4]Patent: US2436645,1944, .

2
[ 40915-37-5 ]
5,6-dihydro-4<i>H</i>-pyran-3-carboxylic acid-(4-bromo-phenacyl ester) [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1952,p. 808,812.

3
[ 40915-37-5 ]
[ 680973-69-7 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

4
[ 83124-87-2 ]
[ 40915-37-5 ]

References: [1]Synthesis,1986,p. 1016 - 1017.
[2]Marine Drugs,2013,vol. 11,p. 5159 - 5189.

5
[ 109317-74-0 ]
[ 40915-37-5 ]

References: [1]Synthesis,1986,p. 1016 - 1017.

6
[ 26274-19-1 ]
[ 67-56-1 ]
[ 201230-82-2 ]
[ 40915-37-5 ]
[ 86971-83-7 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 8336 - 8340.

7
[ 26274-19-1 ]
[ 201230-82-2 ]
[ 40915-37-5 ]
[ 86971-83-7 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 8336 - 8340.

8
[ 40915-37-5 ]
[ 76354-62-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

9
[ 40915-37-5 ]
2-Azido-3-hydroxymethyltetrahydropyran [ No CAS ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

10
[ 40915-37-5 ]
[ 128371-04-0 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

11
[ 40915-37-5 ]
[ 128371-05-1 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

12
[ 40915-37-5 ]
[ 128371-05-1 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

13
[ 40915-37-5 ]
[ 128371-05-1 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

14
[ 40915-37-5 ]
[ 128371-05-1 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 887 - 890.

15
[ 98198-84-6 ]
[ 40915-37-5 ]

References: [1]New Journal of Chemistry,2008,vol. 32,p. 1354 - 1358.

16
[ 110-87-2 ]
[ 79-37-8 ]
[ 40915-37-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	at 0 - 120℃; for 1.5h;	Synthesis of 3,4-dihydro-2H-pyran-5-carboxylic acid: 3,4-dihydro-2H-pyran-5-carboxylic acid was prepared as described m J.Het.Chem., 2010, 47, p.1171. Oxalyl chloride (7.2 mL, 83 mmol) was cooled to 0 C and 3.4-dihydro-2H- pyrane (5.0 mL, 55.4 mmol) was added. The solution was slowly warmed to ambient temperature and stirring was continued for lh. Excess oxalyl chloride was evaporated in vacuo at 30 C. The mixture was then heated to 120 C for 0.5 h, cooled to ambient temperature, and poured into ice-cold aqueous solution of Na2C03. The alkaline solution was extracted with CH2C12 and then acidified with HC1 (6 M). The aqueous layer was extracted with CH2C12 and the organic solution was dried over MgS04, filtered, and evaporated to yield 3,4-dihydro-2H-pyran-5-carboxylic acid (5.1 g, 67% yield). 1H NMR (300 MHz, CDCI3/TMS): delta 11.4 (br s, 1H), 7.70 (s, 1H), 4.08 (t, J = 5 Hz, 2H), 2.26 (t, J = 7 Hz, 2H), 1.89 (m, 2H).
67%		[0561] Synthesis of 3,4-dihydro-2H-pyran-5-carboxylic acid: [0562] 3,4-dihydro-2H-pyran-5-carboxylic acid was prepared as described in J.Het.Chem., 2010, 47, p. l 171. Oxalyl chloride (7.2 mL, 83 mmol) was cooled to 0 C and 3.4-dihydro-2H-pyrane (5.0 mL, 55.4 mmol) was added. The solution was slowly warmed to ambient temperature and stirring was continued for lh. Excess oxalyl chloride was evaporated in vacuo at 30 C. The mixture was then heated to 120 C for 0.5 h, cooled to ambient temperature, and poured into ice-cold aqueous solution of Na2C03. The alkaline solution was extracted with CH2C12 and then acidified with HC1 (6 M). The aqueous layer was extracted with CH2C12 and the organic solution was dried over MgS04, filtered, and evaporated to yield 3,4-dihydro- 2H-pyran-5-carboxylic acid (5.1 g, 67% yield). 1H NMR (300 MHz, CDC13/TMS): delta 11.4 (br s, 1H), 7.70 (s, 1H), 4.08 (t, J = 5 Hz, 2H), 2.26 (t, J= 7 Hz, 2H), 1.89 (m, 2H).

References: [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 1171 - 1175.
[2]Patent: WO2012/40230,2012,A1 .Location in patent: Page/Page column 99-100.
[3]Patent: WO2013/142269,2013,A1 .Location in patent: Paragraph 0561; 0562.
[4]Chemical Communications,2019,vol. 55,p. 755 - 758.

17
[ 40915-37-5 ]
[ 873397-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Pd/C (30%); In ethanol; at 20℃; for 48h;	Synthesis of tetrahydro-2H-pyran-3-carboxylic acid:<strong>[40915-37-5]3,4-dihydro-2H-pyran-5-carboxylic acid</strong> (5.0 g, 39 mmol) was hydrogenated with H2 under Pd/C (30percent, 500 mg) in EtOH (100 mL) for 2 days at room temperature. The solution was filtered, EtOH was evaporated, and crude tetrahydro-2H-pyran-3-carboxylic acid (4.5 g) was used for next step without purification. 1H NMR (300 MHz, CDCI3/TMS): delta 11.0 (br s, 1H), 4.00 (m, 1H), 3.78 (m, 1H), 3.60 (1H), 3.45 (m, 1H), 2.59 (m, 1H), 1.99 (m, 1H), 1.76-1.59 (m, 3H).
	With Pd/C (30%); hydrogen; In ethanol; at 20℃; for 48h;	[0563] Synthesis of tetrahydro-2H-pyran-3-carboxylic acid: [0564] <strong>[40915-37-5]3,4-dihydro-2H-pyran-5-carboxylic acid</strong> (5.0 g, 39 mmol) was hydrogenated with H2 under Pd/C (30percent, 500 mg) in EtOH (100 mL) for 2 days at room temperature. The solution was filtered, EtOH was evaporated, and crude tetrahydro-2H-pyran-3-carboxylic acid (4.5 g) was used for next step without purification. 1H NMR (300 MHz, CDCI3/TMS): delta 11.0 (br s, 1H), 4.00 (m, 1H), 3.78 (m, 1H), 3.60 (1H), 3.45 (m, 1H), 2.59 (m, 1H), 1.99 (m, 1H), 1.76-1.59 (m, 3H).

References: [1]Patent: WO2012/40230,2012,A1 .Location in patent: Page/Page column 100.
[2]Patent: WO2013/142269,2013,A1 .Location in patent: Paragraph 0563; 0564.

18
[ 40915-37-5 ]
2,5-dioxopyrrolidin-1-yl tetrahydro-2H-pyran-3-carboxylate [ No CAS ]

References: [1]Patent: WO2012/40230,2012,A1 .

19
[ 40915-37-5 ]
[ 98198-84-6 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 5308 - 5311.
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 1484 - 1488.
[3]European Journal of Organic Chemistry,2017,vol. 2017,p. 2280 - 2289.
[4]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2241 - 2246.
[5]Chemical Communications,2019,vol. 55,p. 755 - 758.

20
[ 40915-37-5 ]
[ 1428858-50-7 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 5308 - 5311.

21
[ 40915-37-5 ]
[ 1428858-71-2 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 5308 - 5311.
[2]Chemical Communications,2019,vol. 55,p. 755 - 758.

22
[ 40915-37-5 ]
N-((3-((3,4-trans)-1-benzyl-4-methylpyrrolidin-3-yl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)methyl)tetrahydro-2H-pyran-3-carboxamide [ No CAS ]

References: [1]Patent: WO2013/142269,2013,A1 .

23
[ 40915-37-5 ]
2-((3,4-trans)-1-benzyl-4-methylpyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-3-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one [ No CAS ]

References: [1]Patent: WO2013/142269,2013,A1 .

24
[ 40915-37-5 ]
[ 1369515-37-6 ]

References: [1]Patent: WO2013/142269,2013,A1 .

25
[ 40915-37-5 ]
C₁₉H₂₄O₅ [ No CAS ]