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[ CAS No. 130312-00-4 ]

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2D
Chemical Structure| 130312-00-4
Chemical Structure| 130312-00-4
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Product Details of [ 130312-00-4 ]

CAS No. :130312-00-4MDL No. :MFCD09475810
Formula : C9H14O3 Boiling Point : 249°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :170.21Pubchem ID :-
Synonyms :

Computed Properties of [ 130312-00-4 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 130312-00-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 130312-00-4 ]

  • Upstream synthesis route of [ 130312-00-4 ]
  • Downstream synthetic route of [ 130312-00-4 ]

[ 130312-00-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 130312-00-4 ]
  • [ 103260-44-2 ]
YieldReaction ConditionsOperation in experiment
100% at 80℃; Ethyltetrahydro-4H-pyran-4-ylacetate was prepared from ethyltetrahydro-4H-pyran-4-ylideneacetate (16.0 g, 94 mmol) and Pd/ NH4COOH at 80° C. Colorless oil, Yield: 16.3 g, quantitaive), MS: 173.2 (M+H)+
99% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; b) To a solution of 425 mg (2.5 mmol) of ethyl 2-(dihydro-2H-pyran-4(3H)- ylidene)acetate in 15 mL of MeOH, 133 mg of Pd on carbon 10percent was added. Hydrogen atmosphere was set (1 atm, with a balloon) and the reaction was stirred at room temperature overnight. It was filtered through a pad of celite washing with abundant EtAcO. After removing the solvent the desired compound ethyl 2- (tetrahydro-2H-pyran-4-yl)acetate was obtained as a colorless oil (99percent).
94% With palladium on activated charcoal; hydrogen In methanol at 16 - 19℃; for 18 h; A mixture of ethyl 2-(dihydro-2H-pyran-4(3H)-ylidene) acetate (21 g, 123 mmol) and dry Pd/C (2.5 g) in methanol (300 mE) was stirred at 16-19° C. for 18 h under H2 (30 psi). TEC (petroleum ether:ethyl acetate=3:1) showed no starting material remaining. The mixture was filtered and the filtrate was concentrated under reduced pressure to give crude ethyl5 2-(tetrahydro-2H-pyran-4-yl)acetate (20 g, 94percent) as an oil, which was used for the next step directly without further purification. ‘H NMR (CDC13, 400 MHz): ö 4.11-4.15 (q, J=7.2 Hz, 2H), 3.93-3.95 (d, J=10.8 Hz, 2H), 3.37-3.43 (t, J=11.6 Hz, 2H), 2.23-2.25 (d, J=6.8 Hz, 2H), 1.99-2.03 (m,10 1H), 1.62-1.65 (m, 2H), 1.32-1.36 (m, 2H), 1.24-1.27 (t, J=7.2 Hz, 3H).
84% With sodium tetrahydroborate; nickel dichloride In methanol at 0℃; for 0.5 h; To a solution of ethyl 2-(tetrahydro-4H-pyran-4-ylidene)acetate (0.4 g, 2.33 mmol) in methanol (5 ml) was added NaBH4 (0.198 g, 5.29 mmol) portionwise at 0 °C. After 30 mm of stirring at 0 °C NiC12 (0.12 g, 0.505 mmol) was added slowly. After stirring for 45mm the reaction solvent was evaporated under reduced pressure and diluted with water (10 ml) and the product was extracted with ethyl acetate (3x 10 ml). The combined organic layer was concentrated under reduced pressure to afford the title compound (84percent). ‘H NMR (400MHz, CDC13) & 4.18-4.13 (q, 1=7.2Hz, 2H), 3.99-3.95 (m, 2H), 3.46-3.40 (m, 2H), 2.27-2.25 (m, 2H), 2.10-1.98 (m, 1H), 1.64 (s, 2H), 1.41-1.23 (m, 5H).
78% With palladium 10% on activated carbon; ammonium formate In methanol at 70℃; for 15 h; To a mixture composed of ethyl 2-(2H-pyran-4(3H,5H,6H)-ylidene)acetate (10 g, 58.75 mmol) and ammonium formate (37 g, 587.54 mmol) in methanol (150 ml) was added 10percent Pd-carbon (1.0 g) at room temperature, and the mixture was stirred at 70 °C for 15 hr. The reaction mixture was allowed to cool to room temperature, and the catalyst was collected by filtration through Celite pad and was washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 94:6) to give the title compound as an oil (7.9 g, yield 78percent). 1H-NMR (400 MHz, CDCl3): δ (ppm) 4.13 (q, J = 7.2 Hz, 2H ), 3.97-3.93 (m, 2H), 3.44-3.38 (m, 2H), 2.24 (d, J = 7.2 H z, 2H), 2.08-1.92 (m, 1H) 1.66-1.62 (m, 2H), 1.40-1.29 (m, 2H), 1.26 (t, J = 7.2 Hz, 3H); MS (ESI): m/z 172 (M+).

Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6255 - 6269
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 23, p. 6309 - 6323
[3] Patent: US6340691, 2002, B1, . Location in patent: Page column 66
[4] Patent: EP1147080, 2004, B1, . Location in patent: Page 49
[5] Patent: WO2013/37960, 2013, A1, . Location in patent: Page/Page column 76
[6] Journal of Organic Chemistry, 2006, vol. 71, # 26, p. 9909 - 9911
[7] Patent: US2004/220214, 2004, A1,
[8] Bioscience, Biotechnology, and Biochemistry, 1994, vol. 58, # 4, p. 647 - 651
[9] Patent: US9481674, 2016, B1, . Location in patent: Page/Page column 31; 32
[10] Patent: WO2016/44626, 2016, A1, . Location in patent: Paragraph 00484
[11] Patent: EP2737900, 2014, A1, . Location in patent: Paragraph 0114; 0116-0117
[12] Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 80[13] Chem.Abstr., 1940, p. 4396
[14] Journal of Medicinal Chemistry, 1993, vol. 36, # 16, p. 2300 - 2310
[15] Patent: US2011/144105, 2011, A1, . Location in patent: Page/Page column 54
[16] Patent: WO2016/61160, 2016, A1, . Location in patent: Paragraph 00105
  • 2
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Reference: [1] Patent: EP1019398, 2004, B1, . Location in patent: Page 44
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