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CAS No. : | 3174-74-1 | MDL No. : | MFCD17171194 |
Formula : | C5H8O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MUGSKSNNEORSJG-UHFFFAOYSA-N |
M.W : | 84.12 | Pubchem ID : | 520540 |
Synonyms : |
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 24.65 |
TPSA : | 9.23 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.27 cm/s |
Log Po/w (iLOGP) : | 1.68 |
Log Po/w (XLOGP3) : | 0.77 |
Log Po/w (WLOGP) : | 0.96 |
Log Po/w (MLOGP) : | 0.62 |
Log Po/w (SILICOS-IT) : | 1.66 |
Consensus Log Po/w : | 1.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.85 |
Solubility : | 12.0 mg/ml ; 0.142 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.54 |
Solubility : | 24.0 mg/ml ; 0.286 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.43 |
Solubility : | 31.3 mg/ml ; 0.372 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.57 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P233-P235-P240-P241-P242-P243-P260-P261-P264-P271-P280-P302+P352-P303+P361+P353-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P370+P378-P403-P403+P233-P403+P235-P405-P501 | UN#: | 1993 |
Hazard Statements: | H225-H315-H319-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.44% | To a solution of tetrahydro-4-pyranol (30.00 g) in CH2C12 (250 mL) was added Et3N (35.68 g) at rt, and methylsulfonyl chloride (36.84 g) dropwise at 0 C under N2. The reaction mixture was stirred at 0 C for 1 h, then heated to room temperature and stirred for 12 h. The reaction mixture was quenched with water, washed with water and brine, and dried over anhydrous Na2S04. The mixture was filtered and evaporated in vacuo to give the crude product. A mixture of the residue and DBU (50 mL) was heated at 100 C for 3 h. The resulted mixture was distilled under normal pressure, the fraction of 150-160C was collected to afford the title compound ( 17.40 g, 70.44 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 85.1 (M+l). | |
70.44% | To a solution of tetrahydro-4-pyranol (30.00 g) in CH2Cl2 (250 mL) was added Et3N (35.68 g) at rt, and methylsulfonyl chloride (36.84 g) dropwise at 0 C. under N2. The reaction mixture was stirred at 0 C. for 1 h, then heated to room temperature and stirred for 12 h. The reaction mixture was quenched with water, washed with water and brine, and dried over anhydrous Na2SO4. The mixture was filtered and evaporated in vacuo to give the crude product. A mixture of the residue and DBU (50 mL) was heated at 100 C. for 3 h. The resulted mixture was distilled under normal pressure, the fraction of 150-160 C. was collected to afford the title compound (17.40 g, 70.44%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 85.1 (M+1). | |
3,6-dihydro-2H-pyranTetrahydro-4-pyranol (1005.2g), DCM (5530ml) and triethylamine (1640ml) were combined and cooled to 1 C. Mesyl chloride (1243.8g) was added to the cooled and stirred mixture in a controlled manner over ~2.5h maintaining the temperature below 15C. The mesyl chloride was washed in with DCM (500ml) and the reaction allowed to warm to ambient temperature overnight. The mixture was treated with aqueous ammonium chloride (~2I, 9.8% w/w), stirred for 5min and the phases separated. The organic phase was washed with aqueous ammonium chloride (-2I, 9.8% w/w), water (~2I) and dried (sodium sulphate). The organic phase was concentrated in vacuo (39C, ~15mbar) to an oil which rapidly solidified on standing (1733.9g). This material was treated slowly with DBU (-30OmI) at 52C, over 30min a solution formed and this was treated with DBU (1.71) and the mixture warmed to ~100C (external temperature) over 1 h and maintained at this temperature for 2h. The temperature was raised slowly to 148C (external) and the distilling 3,6-dihydro-2H-pyran collected (527.5g).1 H NMR (400MHz, CDCI3): deltaH 5.85 (1 H, m), 5.72 (1 H, d), 4.13(2H, m), 3.79(2H, t), 2.14(2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydroxide; In water; at 90℃; for 18h; | Preparation 203,6-Dihydro-2H-pyran4-Bromotetrahydropyran (20 g, 121 mmol) and 5 N sodium hydroxide (30 mL) are stirred and heated at 90 C for 18 h. The mixture is cooled to room temperature and the organic layer is separated from the aqueous. The organic layer, containing product only, is poured into a pre-weighed flask containing sodium sulfate for drying, which yields the title compound as a pale yellow oil (9.99 g, 98%). The title compound is stored over sodium sulfate as volatility prevents any filtering, rinsing, and concentration in vacuo. 1H NMR (400 MHz, DMSO-de) delta 5.78-5.74 (m, 1H), 5.69-5.66 (m, 1H), 3.96-3.94 (m, 2H), 3.61 (t, J= 5.5 Hz, 2H), 2.01-1.99 (m, 2H). |
With sodium hydroxide; at 90℃; for 27h; | 3,6-dihydro-2H-pyranSodium hydroxide (10N, 1745ml) was added to 4-bromotetrahydro-2H-pyran (1133.7g), the mixture warmed to 900C with stirring and stirred at ~90C for 27h. The mixture was allowed to cool to ambient temperature, 1800ml of the aqueous phase was separated and the bulk of the organic phase collected. The remaining aqueous phase plus a small volume of the organic phase and the interfacial material was washed with water (20ml), filtered and the filtrate washed with sodium hydroxide solution (10N, 5ml). The organic phase was separated and added to the bulk of material to give 3,6-dihydro-2H-pyran (242.2g).1 H NMR (400MHz, CDCI3): deltaH 5.85 (1 H, m), 5.72 (1 H, d), 4.13(2H, m), 3.79(2H, t), 2.14(2H, m). | |
With sodium hydroxide; at 90℃; for 24h; | Step 1: To 4-bromotetrahydro-2H-pyran (10 g) in round bottom flask was added 10 N NaOH (15 ml). After heated at 90 C for 24 h, the aqueous layer was separated out leaving 3,6- dihydro-2H-pyran as the crude material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 19h; | Preparation 214,7-Dioxabicyclo[4.1.0]heptane MCPBA (29.28 g, 130.6 mmol, 77 wt/wt%) is added to a solution of 3,6-dihydro-2H- pyran (9.99 g, 118.8 mmol) in dichloromethane (100 mL) at 0 C and stirred for 1 h before allowing to warm to room temperature and stirring for 18 h. A saturated aqueous solution of sodium bicarbonate is carefully added and the mixture stirred vigorously. The organic layer is separated from the aqueous, dried over sodium sulfate, filtered, and concentrated in vacuo to yield the title compound (9.7 g, 82%). 1H NMR (400 MHz, DMSO-d6) delta 3.84 (dd, J= 2.7, 13.4 Hz, 1H), 3.74-3.70 (m, 1H), 3.38-3.26 (m, 3H), 3.10-3.09 (m, 1H), 1.87-1.82 (m, 2H). |
76% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step 2) 3.7-dioxabicyclo|"4.1.0"|heptane [0239] To a suspension of m-CPBA (25.6 g, 296 mmol) in DCM (200 mL) was added 3,6-dihydro-2H-pyran (8.3 g, 98.7 mmol) dropwise at 0 C. The reation was stirred at rt overnight, then concentrated in vacuo, and the residue was diluted with DCM (30 mL). The mixture was cooled to 0 C and filtered. The filtrate was concentrated in vacuo to give the title compound as colorless oil (7.5 g, 76%). GC-MS m/z: 100 (M). |
With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 13 - 20℃; | 1,5:3,4-dianhydro-2-deoxypentitolTo a suspension of mCPBA (71.1 %, 1524.2g) in chloroform (4.22I) at 130C was added 3,6-dihydro-2H-pyran (526.5g) over ~2h washing solid down from vessel neck at intervals with portions of chloroform (total -1.51). A further portion of chloroform (0.51) was added and the reaction mixture stirred at 150C for 2.25h. The reaction mixture was warmed to 2O0C over 40min and stirred at 2O0C overnight. The reaction mixture was cooled to O0C, filtered and the solid washed with chilled chloroform (3.50C, 1055ml). The combined filtrate and washings were washed with aqueous sodium carbonate (20% w/w, 1582ml), the phases separated and the organic phase treated with sodium sulphite (1 kg). The organic was filtered and concentrated in vacuo (250C, 150mbar) to give the title compound (506g). The solvent from the in vacuo concentration was re-concentrated in vacuo to yield a second portion of the title compound (41.2g).1 H NMR (400MHz, D6-DMSO): deltaH 3.91 (1 H1 d), 3.77(1 H, d), 3.35-3.29(3H, m partially obscured by water), 3.15(1 H, s), 1.87(2H, m). |
3.3 g | With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 - 20℃; for 16h; | Step 2: To a solution of 3,6-dihydro-2H-pyran in CHCl3 (40 ml) at 0 C was added mCPBA (16 g, 60 mmol). After stirred at 0 C for 1 h, it was warmed up to room temperature and stirred for 15 h. Solid was filtered off, and the filtrate was diluted with more CHCl3, organic layer was washed with Sat. NaHCO3, Na2S2O3, brine, dried and concentrated to give 3,7-dioxabicyclo{4.1.0]heptanes (3.3 g). |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25℃; for 21h; | Step 3: (1 SR, 6RS)-3,7-Dioxa-bicyclo[4.1.0]heptane To a solution of 3,6-dihydro-2H-pyran (6 g, 71.4 mmol,) in CH2Cl2 (300 ml) was added 3-chloroperbenzoic acid (25 g, 107.1 mmol) portionwise at 25 C., and stirred at that temperature for 21 hrs. The resultant white suspension was diluted with water (250 ml) and then with aqueous solution of Na2SO3. The mixture was stirred at 25 C. for 10 min, then basified by addition of saturated aqueous solution of NaHCO3. The organic layer was separated, and the aqueous layer was re-extracted with CH2Cl2. The combined organic layers were washed with saturated aqueous solution of NaHCO3 (100 ml), and brine (80 ml), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the title compound (5 g, 70%; crude) as yellow liquid. | |
4.7 g | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; | Step 3: 3,7-dioxa-bicyclo[4.1.0]heptane: [00303] To a solution of mCPBA (23.5 g, 136.2 mmol) in DCM (15 mL) was added a solution of 3,6-dihydro-2H-pyran (5.7 g, 68.1 mmol) in DCM (10 mL), and this mixture was stirred at ambient temperature for 6 h. The reaction was monitored by 1H NMR, and when incomplete, additional mCPBA (11.8 g, 68.1 mmol) was added followed by stirring at room temperature overnight. Next, the reaction mixture was filtered, and the filtrate was washed with saturated 112 ABV12212USO1 aqueous Na2SO3, NaHCO3, and water. The organic fraction was dried over Na2SO4, filtered and concentrated in vacuo to afford the titled compound, 4.7 g. |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 22h; | To a solution of m-chloroperbenzoic acid (23.51 g, 136.2 mmol, 2 eq.) in DCM (15 mL) is added a solution of 3,6-dihydro-2H-pyran (5.73 g, 68.1 mmol, 1 eq.) in DCM (10 mL). The reaction mixture is allowed to stir at r.t. for 6 h, after which m-chloroperbenzoic acid (11.76 g, 68.1 mmol, 1 eq.) is added. The reaction mixture is stirred at r.t. for 16 h and filtered off. The filtrate is washed with saturated solutions of Na2SO3, NaHCO3, and water. The organic layer is then dried over Na2SO4, filtered and concentrated in vacuo to afford the desired compound, used in the next step without further purification. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 22h; | To a solution of m-chloroperbenzoic acid (23.51 g, 136.2 mmol, 2 eq.) in DCM (15 mL) is added a solution of 3,6-dihydro-2H-pyran (5.73 g, 68.1 mmol, 1 eq.) in DCM (10 mL). The reaction mixture is allowed to stir at r.t. for 6 h, after which m-chloroperbenzoic acid (11.76 g, 68.1 mmol, 1 eq.) is added. The reaction mixture is stirred at r.t. for 16 h and filtered off. The filtrate is washed with saturated solutions of Na2S03, NaHCOs, and water. The organic layer is then dried over Na2SO i, filtered and concentrated in vacuo to afford the desired compound, used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.52% | With pyridinium chlorochromate; In dichloromethane; for 8h;Reflux; | To a solution of <strong>[3174-74-1]3,6-dihydro-2H-pyran</strong> (4.00 g, 1 eq) in CH2C12 (150 mL) was added PCC (1.2 eq). The mixture was heated to reflux for 4 h, to the mixture was added PCC (0.6 eq) additional. The reaction mixture was refluxed for another 4 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 2: 1 (v/v) PE/EA) to give the title compound as colorless oil (0.77 g, 16.52 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 99(M+1); ? NMR (400MHz, CDC13) ?: 2.44-2.49 (m, 2H), 4.42-4.45 (m, 2H), 6.02-6.05 (m, 1 H), 6.93-6.97 (m, 1 H) ppm. |
16.52% | With pyridinium chlorochromate; In dichloromethane; for 8h;Reflux; | To a solution of <strong>[3174-74-1]3,6-dihydro-2H-pyran</strong> (4.00 g, 1 eq) in CH2Cl2 (150 mL) was added PCC (1.2 eq). The mixture was heated to reflux for 4 h, to the mixture was added PCC (0.6 eq) additional. The reaction mixture was refluxed for another 4 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to give the title compound as colorless oil (0.77 g, 16.52%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 99 (M+1); 1H NMR (400 MHz, CDCl3) delta: 2.44-2.49 (m, 2H), 4.42-4.45 (m, 2H), 6.02-6.05 (m, 1H), 6.93-6.97 (m, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13 g | With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 80℃; | A solution of <strong>[134419-59-3]tetrahydro-2H-pyran-4-yl methanesulfonate</strong> (45.0 g) in 1, 8-diazabicyclo [5. .0] undec-7-ene (100 mL) was stirred at 80C overnight. The reaction solution was allowed to cool to room temperature and evaporated under reduced pressure (10 mmHg) to give the title compound (13.0 g) .¾ NMR (400 MHz, CDC13) delta 2.11-2.17 (2H, m) , 3.80 (2H, t, J = 6.0 Hz), 4.12-4.14 (2H, m) , 5.70-5.74 (1H, m) , 5.82-5.87 (1H, m) . |
6 g | With 1,8-diazabicyclo[5.4.0]undec-7-ene; under 760.051 Torr;Heating; | A mixture of <strong>[134419-59-3]tetrahydro-2H-pyran-4-yl methanesulfonate</strong> (20 g, 111 mmol) and DBU (18.8 ml, 125.6 mmol) was distilled under normal atmospheric pressure. The fraction at 90 - 96C was 6- dihydro-2H-pyran (6 g, 64%) as a colourless liquid. |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; under 760.051 Torr; | Step 2: 3, 6-Dihydro-2H-pyranA mixture of <strong>[134419-59-3]tetrahydro-2H-pyran-4-yl methanesulfonate</strong> (20 g, 111 mmol) and DBU (18.8 ml, 125.6 mmol) was distilled under normal atmospheric pressure. The fraction at 90 - 96C was 6-dihydro-2H-pyran (6 g, 64%) as colourless liquid. |
6 g | With 1,8-diazabicyclo[5.4.0]undec-7-ene; under 760.051 Torr;Reflux; | A mixture of <strong>[134419-59-3]tetrahydro-2H-pyran-4-yl methanesulfonate</strong> (20 g, 111 mmol) and DBU (18.8 ml, 125.6 mmol) was distilled under normal atmospheric pressure. The fraction at 90-96 C. was 6-dihydro-2H-pyran (6 g, 64%) as colourless liquid. |
5.7 g | With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 90 - 150℃; for 6h; | Step 2: 3,6-dihydro-2H-pyran: [00302] DBU (16.4 mL) was added to methanesulfonic-acid-tetrahydro-pyran-4-yl ester (16.4 g, 90.9 mmol), and the mixture was heated from 90 C to 150 C over 1 h and then 5 h at 150 C. 1H NMR showed that the starting material was consumed and desired compound was formed. The titled compound was collected from the reaction mixture using distillation at 70-75 C, 5.7 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | 3'-methoxy-4'-tetrahydropyranylacetophenone (THP-C). In an oven-dried, 500 mL round bottom flask equipped with a stir bar and an addition funnel, p-toluenesulfonic acid monohydrate (156 mg, 0.82 mmol), pyridine (66 muL, 0.82 mmol), acetovanillone (6.10 g, 36.7 mmol), and CH2Cl2 (170 mL) were combined and rapidly stirred. Dihydropyran (10 mL, 110 mmol) was diluted with 40 mL of CH2Cl2, poured into the addition funnel, and added drop wise to the acetovanillone solution over a period of 2 h. The reaction was stirred for an additional 12 h at room temperature, after which it was washed with 200 mL of 1.0 N NaOH (2*). The organic phase was dried over Na2SO4, filtered, and concentrated to a clear oil under reduced pressure. The oil crystallized upon standing to afford 4.2 g of THP-C as a white solid (46% yield). The solid was used without further purification. TLC: Rf=0.19 (hexane/EtOAc 4:1); Melting point: 67-69 C.; 1H NMR: (300 MHz, CDCl3) delta 7.52 (s, 1H), 7.50 (d, J=10 Hz, 1H), 7.13 (d, J=8 Hz, 1H), 5.50 (t, J=3 Hz, 1H), 3.90 (s, 3H), 3.89 (m, 1H), 3.59 (m, 1H), 2.54 (s, 3H), 1.95 (m, 3H), 1.63 (m, 1H); 13C NMR: (75 MHz, CDCl3) delta 197.08, 150.92, 150.12, 131.60, 123.18, 115.65, 111.29, 97.14, 62.31, 56.32, 30.33, 26.45, 25.31, 18.79; IR (ATR): 2966, 2936, 2880, 1672, 1585, 1510, 1462, 1442, 1413, 1390, 1352, 1290, 1272, 1243, 1221, 1201, 1172, 1153, 1120, 1110, 1051, 1032, 1020, 959 1046 cm-1; ESI-MS: expected, 250.1; observed, m/z 251.1 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
sulfuric acid; In tetrahydrofuran; at 20℃; | To a suspension of [4- [L- (4-HYDROXY-PHENYL)-IH-BENZOIMIDAZOL-2-YL]-BENZOIC] acid methyl ester (0.150 g, 0.436 [MMOL)] of 2,3-<strong>[3174-74-1]dihydropyran</strong> (0. [5MUT)] was added two drops of concentrated sulfuric acid. To the reaction material was added THF [(3ML)] and the mixture was stirred at room temperature under nitrogen over night. The reaction material was diluted with ethyl acetate (30ml) and washed with saturated sodium bicarbonate and brine. The organic phase was dried (MgS04) and concentrated by vacuum. The residue was purified by silica gel chromatography to give [4- {1- [4-] [(TETRAHYDRO-PYRAN-2-YLOXY)-PHENYL]-1H-BENZOIMIDAZOL-2-YL}-BENZOIC] acid methyl ester (0. [151 G,] 0.352 [MMOL).] MS (MH)+ 429; 1H NMR [CDCI3) No.H 7. ]94-7.96 (d, 2H), 7.85- 7.87 (d, [1H),] 7.64 (d, 2H), 7.12-7. 34 (m, 7H), 5.44-5. 46 (m, [1H), 3. 89-6.] 93 (m, [1H),] 3.88 (s, 3H), 3.63-3. 66 (m, [1H),] 1.61-2. 02 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In ethyl acetate; at 50℃; for 0.5h;pH 7.0;Heating / reflux; | 2,6-Dichloro-9H-purine (20 g, 0.11 mol) and 4-toluenesulphonic acid monohydrate (0.2 g) were dissolved in ethyl acetate (300 ml), the mixture was heated to 50 C. and a solution of 2,3-<strong>[3174-74-1]dihydropyran</strong> (12.6 ml, 0.14 mol) in ethyl acetate (50 ml) was added slowly over 30 min. The reaction mixture was then cooled to room temperature, water (100 ml) was added and the pH of the solution was adjusted to 7 with a saturated aqueous solution of sodium hydrogen carbonate. The layers were separated and the organic layer was washed sequentially with water and brine, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residue was azeotroped from pentane (×2) to afford the title compound as a slightly impure white solid (30.9 g) 1H-NMR (CDCl3) delta: 8.30 (1H, s), 5.75 (1H, dd), 4.25-4.15 (1H, m), 3.85-3.70 (1H, m), 2.20-1.60 (6H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridinium p-toluenesulfonate; In dichloromethane; at 22℃; for 18h; | A suspension of [8- (BENZYLOXY)-5- [ (IR)-2-BROMO-L-HYDROXYETHYL] QUINOLIN-2 (LH)-ONE] [(100MG)] and pyridinium tosylat [(14MG)] in dry DCM [(2ML)] was treated with 2,3- dihydropyran (61. [2, U1)] and stirred at [22C] for 18h. The reaction mixture was concentrated in vacuo and purified by chromatography (Hexane-EtOAc 2: 1, biotage) to give the title compound (77mg). Rf [EtOAc-Hexane (1: 1) ] 0.54 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 18h; | To 13. 6ML of methylene chloride, there were added 3.19g (13. 62MMOL, LEQ. ) OF THE ABOVE-OBTAINED CRUDE PRODUCT OF OPTICALLY ACTIVE METHYL- (S)-4-TRIFLUOROMETHYLMANDELATE, 1.72g (20. 45MMOL, 1. 50EQ.) OF <strong>[3174-74-1]DHP</strong>, and 0.04g (0.16mmol, 0. 01EQ.) of PPTS, followed by stirring at room temperature for 18HR. After the reaction, a saturated sodium hydrogencarbonate aqueous solution was added to the reaction liquid, followed by extraction with ethyl acetate. The recovered organic layer was washed with saturated brine, followed by drying with anhydrous sodium sulfate, filtration, concentration and vacuum drying, thereby obtaining 4.33g of a crude product of optically active, THP-protective METHYL- (S)-4-TRIFLUOROMETHYLMANDELATE represented by the following formula. The yield was 100%. NMR data are as follows. 1H-NMR (standard substance: TMS ; solvent : CDC13), 8ppm : 1.40-2. 05 (m, 6H), 3.40-3. 60 (m, 1H), 3.60-3. 70 (m, 0.5H), 3.73 (s, 3H), 3. 85-4. 00 (m, 0.5H), 4.58 (t, 0. 5H), 4.91 (t, 0.5H), 5.29 (s, 0.5H), 5.39 (s, 0.5H), 7.56-7. 67 (d, d, s, Ar-H, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With toluene-4-sulfonic acid; at 0℃; for 1h; | A solution of 22 gm (177.4 mMol) 3-methoxyphenol in 30 mL <strong>[3174-74-1]dihydropyran</strong> was added dropwise to a solution of 100 mg (0.525 mMol) p-toluenesulfonic acid monohydrate in 10 mL <strong>[3174-74-1]dihydropyran</strong> while cooling in an ice/water bath. After stirring for 1 hour the reaction mixture was diluted with 300 mL diethyl ether and then washed sequentially with 100 mL 0.1 N sodium hydroxide and 100 mL saturated aqueous sodium chloride. The remaining organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The resulting oil was distilled. The fraction distilling at 110-130 C. was collected and then partitioned between 5 N sodium hydroxide and diethyl ether. The organic phase was separated, washed sequentially with water and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to provide 27.1 gm (73%) of tetrahydropyran-2-yl 3-methoxyphenyl ether.1H-NMR(CDCl3): delta 7.18 (t, 1H), 6.65-6.60 (m, 2H), 6.50 (dd, 1H), 5.4 (t, 1H), 3.95-3.90 (m, 1H), 3.80 (s, 3H), 3.62-3.55 (m, 1H), 2.0-1.6 (m, 6H). |
Tags: 3174-74-1 synthesis path| 3174-74-1 SDS| 3174-74-1 COA| 3174-74-1 purity| 3174-74-1 application| 3174-74-1 NMR| 3174-74-1 COA| 3174-74-1 structure
[ 17327-22-9 ]
4-Methoxy-3,6-dihydro-2H-pyran
Similarity: 0.71
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