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Chemical Structure| 4295-99-2
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Product Details of [ 4295-99-2 ]

CAS No. :4295-99-2 MDL No. :MFCD08690357
Formula : C6H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :RLZJFTOYCVIYLE-UHFFFAOYSA-N
M.W : 111.14 Pubchem ID :11815837
Synonyms :

Calculated chemistry of [ 4295-99-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.68
TPSA : 33.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 0.29
Log Po/w (WLOGP) : 0.94
Log Po/w (MLOGP) : 0.07
Log Po/w (SILICOS-IT) : 1.4
Consensus Log Po/w : 0.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.71
Solubility : 21.6 mg/ml ; 0.194 mol/l
Class : Very soluble
Log S (Ali) : -0.55
Solubility : 31.6 mg/ml ; 0.285 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.8
Solubility : 17.5 mg/ml ; 0.157 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 4295-99-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4295-99-2 ]

* 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 [ 4295-99-2 ]
  • Downstream synthetic route of [ 4295-99-2 ]

[ 4295-99-2 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 4295-99-2 ]
  • [ 130290-79-8 ]
YieldReaction ConditionsOperation in experiment
85.3% With ammonia; hydrogen In methanol at 45 - 60℃; for 5 - 17 h; Example 43
(Synthesis of 4-aminomethyltetrahydropyran)
In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 50.0 g of 22percent by weight ammonia-methanol solution and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61MPa) at 45 to 55°C for 17 hours under stirring.
After completion of the reaction, insoluble materials were filtered, and the filtrated material was washed with 30 ml of methanol.
The filtrate and the washed solution were combined and concentrated under reduced pressure, and then, the concentrate was distilled under reduced pressure (73 to 74°C, 2.67 kPa) to tive 7.94 g (Isolation yield; 76.6percent) of 4-aminomethyltetrahydropyran as colorless liquid.
Physical properties of the 4-aminomethyltetrahydropyran are as follows.
1H-NMR (DMSO-d6, δ (ppm)); 1.02 to 1.16 (2H, m), 1.10 to 1.50 (2H, brs), 1.34 to 1.45 (1H, m), 1.56 to 1.61 (2H, m), 2.39 (2H, d, J=6.3Hz), 3.20 to 3.29 (2H, m), 3.81 to 3.86 (2H, m)
CI-MS (m/e); 116 (M+1), 99
Example 45 (Synthesis of 4-aminomethyltetrahydropyran) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 100 ml of 22percent by weight ammonia methanol solution and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61MPa) at 50 to 60°C for 5 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtered material was washed with 30 ml of methanol, and the filtrate and the washed solution were combined. When this solution was analyzed by gas chromatography (Internal standard method), 8.84 g (Reaction yield: 85.3percent) of 4-aminomethyltetrahydropyran was found to be formed. Incidentally, bis(4-tetrahydropyranylmethyl)amine which is a by-product was not formed.
52.7% With hydrogen In methanol at 50 - 60℃; for 5 h; Comparative example 1 (Synthesis of 4-aminomethyltetrahydropyran) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 100 ml of methanol and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61 MPa) at 50 to 60°C for 5 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtered material was washed with 30 ml of methanol, and the filtrate and the washed solution were combined. When this solution was analyzed by gas chromatography (Internal standard method), 7.19 g (Reaction yield: 52.7percent) of the 4-aminomethyltetrahydropyran was found to be formed. Incidentally, 4.28 g of bis(4-tetrahydropyranylmethyl)amine which is a by-product was formed.
60 g With ammonia; hydrogen In methanol at 40 - 45℃; for 12 h; 4-Cyano-tetrahydropuran(500 mL) in methanolic ammonia (200 mL) was hydrogenated in the presence of Raney nickel (10 g) under a pressure of 4 to 5 kg/cm2 hydrogen gas for 12hours at 45 After cooling, the reaction solution was filtered through a Celite bed. The reaction mixture was distilled at 55 °C to provide the desired product (60 g, Yield: 0.60 w/w).
Reference: [1] Patent: EP1671937, 2006, A1, . Location in patent: Page/Page column 16-17
[2] Patent: EP1671937, 2006, A1, . Location in patent: Page/Page column 17
[3] Justus Liebigs Annalen der Chemie, 1938, vol. 535, p. 37,45
[4] Patent: US6372778, 2002, B1, . Location in patent: Example 80
[5] Patent: US2006/63804, 2006, A1, . Location in patent: Page/Page column 13
[6] Patent: EP1671937, 2006, A1, . Location in patent: Page/Page column 16-17
[7] Patent: WO2018/29711, 2018, A2, . Location in patent: Page/Page column 30
  • 2
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  • [ 130290-79-8 ]
Reference: [1] Patent: US5783701, 1998, A,
  • 3
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  • [ 50675-18-8 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With diisobutylaluminium hydride In toluene at -78℃; for 1 h;
Stage #2: With water; ammonium chloride In toluene
Reference Example 2: Tetrahydropyran-4-carbaldehyde. To a solution of tetrahydro pyran-4-carbonitrile (1.0 g, 9.0 mmol) in toluene (10 mL) was added diisobutylaluminium hydride solution (DIBAL-H, 10.8 mL, 10.8 mrnol,10 IM in toluene) at -78°C. The reaction was stirred at -780C for 1 hour then allowed to warm to r.t. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford tetrahydropyran-4-carb aldehyde (530 mg, 52 percent).
Reference: [1] Patent: WO2008/62182, 2008, A1, . Location in patent: Page/Page column 110
  • 4
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  • [ 4295-99-2 ]
YieldReaction ConditionsOperation in experiment
94% for 4 h; Reflux; Inert atmosphere Thionyl chloride (10.0 mL, 137 mmol) was added to oxane-4-carboxamide (3.0 g, 23 mmol) and thereaction mixture was refluxed for 4 h, after which the reaction mixture was poured over ice andbasified to pH 14 with NaOH (50percent). The aqueous solution was extracted with EtOAc (3 × 50 mL),dried (Na2SO4) and concentrated in vacuo to give the product as a pale yellow oil (2.4 g, 94percent). Theproduct obtained did not require any further purification.IR νmax 2961, 2932, 2851, 2240, 1468, 1446, 1390, 1242, 1125, 1066, 1011 cm−1;1H-NMR (CDCl3, 500 MHz): 3.91 (2H, ddd, J 11.9, 6.3, 3.6, 2×2-HA), 3.61 (2H, ddd, J 11.9, 7.8, 3.3,2×2-HB), 2.91–2.85 (1H, m, 4-H), 1.99–1.92 (2H, m, 2×3-HA), 1.91–1.84 (2H, m, 2×3-HB);13C-NMR (CDCl3, 75 MHz): 121.2, 65.6, 28.9, 25.3;HRMS (ESI+): Calculated for C6H10NO ([M+H]+): 112.0756. Found: 112.0754, Δ –1.8 ppm.
90% With thionyl chloride In benzene for 4 h; Heating / reflux A suspension of tetrahydro-2H-pyran-4-carboxamide (4.90 g, 37.9 mmol) in benzene (10 ml) was treated with thionyl chloride (5 ml) and the resulting mixture was stirred at reflux for 4 hours. The cooled mixture was poured onto ice and basified with 50percent potassium hydroxide. The aqueous fraction was saturated with salt and extracted with ethyl acetate. The organic fraction was then dried over anhydrous magnesium sulfate and concentrated. Distillation under reduced pressure gave 3.80 g (90percent yield) of the title nitrile as a clear oil: bp 80-90° C./15 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.91 (4H, m, 2.x.CH2), 2.89 (1H, m, CH), 3.62 (2H, m, OCH2), 3.92 (2H, m, OCH2).
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 11, p. 2629 - 2635
[2] Patent: US2007/111984, 2007, A1, . Location in patent: Page/Page column 45
[3] Journal of the American Chemical Society, 1943, vol. 65, p. 370
[4] Patent: US2009/253679, 2009, A1, . Location in patent: Page/Page column 54-55
  • 5
  • [ 29943-42-8 ]
  • [ 38622-91-2 ]
  • [ 4295-99-2 ]
YieldReaction ConditionsOperation in experiment
73% With potassium <i>tert</i>-butylate In ISOPROPYLAMIDE at -10 - 20℃; for 2 h; Intermediate 11 : 2-(Tetrahydro-2H-pyran-4-yl)-lH-imidazole-5-carbaldehydeStep a: tetrahydro-2H-pyran-4-carbonitrile[0473] A solution of dihydro-2H-pyran-4(3H)-one (10.0 g, 0.1 mol) and TosMIC (25.35 g, 0.13 mol) in DME (75.0 mL) was cooled to -10°C and t-BuOK (28.0 g, 0.25 mol) was added in portions to keep the temperature below 5°C. The reaction mixture was stirred at 0°C for 1 h and then at room temperature for 2 h. The solvent was removed under reduced pressure and the residue was treated with water. The resulting mixture was extracted with ether and the combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by distillation to affordl8 g of the title compound as a light yellow liquid (73percent yield).
47% With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane; ethanol at 0 - 40℃; for 1.5 h; Reference Example 1 : Tetrahvdro-pyran-4-carbonitriIe. To a solution of tetrahydro-pyran-4-one (2.0 g, 20.0 mmol) and tosyl methyl isocyanide (5.06 g, 25.9 mmol) in dimethoxyethane (15 mL) was added ethanol (1.5 niL). The reaction mixture was cooled to 0°C and potassium tert-butoxide (5.57 g, 49.7 mmol) was added. The resulting reaction mixture was warmed to r.t. and stirred for Ih, then heated to 4O0C for 30 minutes. The mixture was cooled to r.t. and filtered. The resulting solid was washed with dimethoxyethane (3 x 15 mL), and the combined filtrates were evaporated to give a crude compound which was purified by column chromotography over 60-120 silica gel using 10-12percent ethyl acetate in hexane to afford 5 tetrahydro-pyran-4-carbonitrile (1.05 g, 47 percent) as a light yellow liquid.
44% With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane; ethanol at 0 - 40℃; for 2 h; t-BuOK (26.9g, 0.24mol) was added over 30min to a solution of tetrahydro-4H-pyran-4-one(1Og, O.lmol) and TOSMIC (25.38g, 0.13mol) in EtOH-DME (1:35 / 36OmL) under argon at00C. The reaction mixture was stirred at 00C for Ih then heated at 4O0C for Ih. On cooling, the precipitated solid was removed by filtration and washed with DME. The combined filtrates were evaporated to dryness and the residue obtained was dissolved in EtOAc (15OmL), washed successively with H2O (15OmL), 5percentKHSO4 (15OmL), saturated NaHCO3 (15OmL), brine(15OmL) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by chromatography (hexane-EtOAc (4:1)) (4.86g, 44percent). 1H NMR (CDCl3) 3.93-3.86 (2H, m), 3.64-3.56 (2H, m), 2.86 (IH, m), 1.98-1.81 (4H, m).
Reference: [1] Patent: WO2012/178015, 2012, A2, . Location in patent: Page/Page column 119
[2] Patent: WO2008/62182, 2008, A1, . Location in patent: Page/Page column 109-110
[3] Patent: WO2007/135417, 2007, A1, . Location in patent: Page/Page column 63
  • 6
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  • [ 177703-80-9 ]
  • [ 4295-99-2 ]
YieldReaction ConditionsOperation in experiment
39% With potassium <i>tert</i>-butylate In monoethylene glycol diethyl ether; <i>tert</i>-butyl alcohol at 20℃; for 3 h; Tetrahydro-2H-pyran-4-carbonitrile. A solution of tetrahydro-4H-pyran-4-one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0° C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39° C. 1.7 mm Hg to give the title compound as a colorless oil (10.87 g, 39percent yield). 1H NMR (300 MHz, CDCl3) δ: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (1H, m), 1.97-1.78 (4H, m).
39% With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane at 0 - 20℃; for 3 h; Tetrahydro-2H-pyran-4-carbonitrile. A solution of tetrahydro-4H-pyran-4-one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0° C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39° C. 1.7 mm Hg to give the title compound as a colorless oil (10.87 g, 39percent yield). 1H NMR (300 MHz, CDCl3) δ: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (1H, m), 1.97-1.78 (4H, m).
Reference: [1] Patent: US2005/256109, 2005, A1, . Location in patent: Page/Page column 12
[2] Patent: US2008/4265, 2008, A1, . Location in patent: Page/Page column 18
  • 7
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YieldReaction ConditionsOperation in experiment
39% With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane; <i>tert</i>-butyl alcohol at 0 - 20℃; for 3.5 h; Intermediate 4Tetrahydro~2H-pyran-4-carbonitrile. A solution of tetrahydro-4Hr-pyran-4- one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0 °C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39 °C 1.7 mm Hg to give the title compound as a colorless oil (10.87 g, 39percent yield). 1H NMR (300 <n="42"/>MHz, CDCl3) δ: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (IH, m), 1.97-1.78 (4H, m).
Reference: [1] Patent: WO2007/58646, 2007, A1, . Location in patent: Page/Page column 39-40
  • 8
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  • [ 243661-09-8 ]
  • [ 4295-99-2 ]
YieldReaction ConditionsOperation in experiment
39% With potassium <i>tert</i>-butylate In ethylene glycol dimethylether; <i>tert</i>-butyl alcohol at 0 - 20℃; for 3.5 h; A solution of tetrahydro-4H-pyran-4-one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0° C.
Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL).
After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3.
The organic phase was dried (Na2SO4) and concentrated.
The residue was distilled at 39° C. 1.7 mm Hg to give the title compound as colorless oil (10.87 g, 39percent yield).
1H NMR (300 MHz, CDCl3) δ: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (1H, m), 1.97-1.78 (4H, m).
Reference: [1] Patent: US2008/306051, 2008, A1, . Location in patent: Page/Page column 15
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Reference: [1] Patent: US2006/63804, 2006, A1, . Location in patent: Page/Page column 13
  • 10
  • [ 97986-34-0 ]
  • [ 4295-99-2 ]
YieldReaction ConditionsOperation in experiment
41% at 80℃; for 7 h; In a glass flask having inner volume of 20 ml provided with stirrer, the thermometer, and the reflux condenser, 2.62 g (10.2mmol) of tetrahydropyranyl 4-p-toluenesulfonate, potassium cyanide 1.0g (15.4mmol), and 10 ml of dimethyl sulfoxide were added and the mixture was reacted at 80 degrees C for 7 hours. After completion of the reaction, the reaction mixture was analyszed by gas chromatography (internal standard method), 0.46 g of 4-cyanotetrahydropyran was obtained (reaction yield: 41percent).
Reference: [1] Patent: JP5673729, 2015, B2, . Location in patent: Paragraph 0066
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  • [ 4295-99-2 ]
YieldReaction ConditionsOperation in experiment
44% at 80℃; for 7 h; In a glass flask having inner volume of 20 ml provided with stirrer, the thermometer, and the reflux condenser, 1.85 g (10.2mmol) of tetrahydropyranyl 4-methanesulfonate, potassium cyanide 1.0g (15.4mmol), and 10 ml of dimethyl sulfoxide were added and the mixture was reacted at 80 degrees C for 7 hours. After completion of the reaction, the reaction mixture was analyszed by gas chromatography (internal standard method), 0.50 g of 4-cyanotetrahydropyran was obtained (reaction yield: 44percent).
Reference: [1] Patent: JP5673729, 2015, B2, . Location in patent: Paragraph 0064
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  • [ 25637-16-5 ]
  • [ 4295-99-2 ]
YieldReaction ConditionsOperation in experiment
9% at 80℃; for 7 h; In a glass flask having inner volume of 20 ml provided with stirrer, the thermometer, and the reflux condenser, 1.69 g (10.2mmol) of 4-bromotetrahydrofuran, potassium cyanide 1.0g (15.4mmol), and 10 ml of dimethyl sulfoxide were added and the mixture was reacted at 80 degrees C for 7 hours. After completion of the reaction, the reaction mixture was analyszed by gas chromatography (internal standard method), 0.10 g of 4-cyanotetrahydropyran was obtained (reaction yield: 9percent).
Reference: [1] Patent: JP5673729, 2015, B2, . Location in patent: Paragraph 0067
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Reference: [1] Patent: US6436964, 2002, B1,
  • 14
  • [ 1768-64-5 ]
  • [ 10442-39-4 ]
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Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 43, p. 13902 - 13907
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Reference: [1] Patent: US6372778, 2002, B1, . Location in patent: Example 80
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Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
[2] Synlett, 2011, # 15, p. 2223 - 2227
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  • [ 52748-35-3 ]
  • [ 4295-99-2 ]
Reference: [1] Synlett, 2011, # 15, p. 2223 - 2227
  • 18
  • [ 362703-30-8 ]
  • [ 4295-99-2 ]
Reference: [1] Patent: WO2018/29711, 2018, A2,
  • 19
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  • [ 344329-76-6 ]
Reference: [1] Patent: CN102993144, 2016, B, . Location in patent: Paragraph 0014; 0015
  • 20
  • [ 4295-99-2 ]
  • [ 67-56-1 ]
  • [ 110238-91-0 ]
YieldReaction ConditionsOperation in experiment
63.5% at 70 - 75℃; for 10 h; Inert atmosphere In a 300 ml glass flask equipped with stirrer, thermometer and reflux condenser, 22.8 g (197.4 mmol) of 4-cyanotetrahydropyran having a purity of 99percent synthesized in Example 5, 60percent (98 mmol) 98percent sulfuric acidas well as130 ml (3.21 mol) of methanol was added under nitrogen atmosphere, the mixture was reacted at 70 to 75°C. for 10 hours with stirring. After completion of the reaction, 100 ml of water was added, the reaction solution was cooled to room temperature. The organic layer and aqueous layer were separated. Then,the aqueous layer was extracted three times with 200 ml of ethyl acetate, the organic layer and the ethyl acetate extract were mixed, and concentrated under reduced pressure. The concentrate thus obtained was distilled under reduced pressure (75 to 76 ° C., 1.2 to 13 kPa) to obtain 18.3 g of methyl tetrahydropyran-4-carboxylate as a colorless liquid having a purity of 98.7percent (area percentage by gas chromatography) (isolation yield: 63.5percent).
Reference: [1] Patent: JP5673729, 2015, B2, . Location in patent: Paragraph 0077
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  • [ 1228779-96-1 ]
Reference: [1] Patent: WO2018/29711, 2018, A2,
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