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CAS No. : | 87776-76-9 | MDL No. : | MFCD06797643 |
Formula : | C10H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 164.20 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
84% | With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 63h; | To a solution of 2-(2,3-dihydro-benzofuran-5-yl)-ethanol (Intermediate 21) (2.12g, 13mmol) in 10OmL dry DCM were added carbon tetrabromide (4.71 g, 14.2mmol) and triphenylphosphine (3.74g, 14.3mmol). The reaction mixture was stirred for 3h at RT, then more carbon tetrabromide (1.94g) and triphenylphosphine (3.38g) were added, and the mixture stirred for 6Oh. The reaction mixture was then concentrated, the residue was triturated with diethyl ether and filtered. The filtrate was purified by silica gel chromatography eluting with DCM to give the title compound as a light yellow oil, that crystallised upon standing. Yield: 2.48g (84percent)1H NMR (CDCI3) delta 3.07 (t, 2H), 3.19 (t, 2H), 3.51 (t, 2H), 3.55 (t, 2H), 6.72 (d, 2H), 6.92 (d, 2H)1 7.04 (s, 1H). |
75.9% | With phosphorus tribromide; In chloroform;Reflux; | 60 g (365 mmol) of compound 2 obtained in Example 8 was added to the reaction flask,Then add 400g of chloroform,A solution of phosphorus tribromide/chloroform (38 g/120 g) was added dropwise via a dropping funnel.After dropping,Heat to reflux for 5-6 hours.After confirming the reaction,Cool down to 20°C,Add 500g of chloroform;120 g of sodium carbonate/1200 g of water solution was added dropwise with stirring.Stir and extract thoroughlyResting,Liquid separation,The aqueous phase was extracted with chloroform (500 g×3).Combine the organic phase,Dry with anhydrous sodium sulfatefilter,The filtrate is concentrated,Get an oil,Add methanol, stir to crystallize,Get a solid,80g.The resulting solid was heated and dissolved with 120 g of methanol.After completely dissolved,filter,Cool crystallization,Obtained solid 63g (theoretical amount: 82.98g);Yield:75.9percent. |
73% | Synthesis of (1) was accomplished using the commercially available piperidine-3-ol (8) according to Scheme 1. The dl-mixture of piperidine-3-ol was resolved according to the method described in JCS Perkin Trans Il (1981), 697 using D (+)-10-camphorsulfonic acid and 3R(+) hydroxypiperidine (+)-10-camphorsulfaonate (2) was obtained after recrystallization. (2) was then converted to 3-(1-carbamoyl-1 ,1-diphenylmethyl)piperidine (6) in four steps using the methods described in European Patent (EP 0 376 358 A1). (6) was EPO <DP n="32"/>then allowed to react with (7) (prepared by a known procedure- Dunn et al, in J. Med Chem (1986) 2236) in the presence of potassium carbonate in acetonitrile at reflux to give (8). Compound (8) was used in the antiviral assay after in-house analysis by proton NMR and LCMS. 1 H NMR (400 MHz, DMSO-d6) delta 7.30 (m, 10H), 7.03 (s, 1H)1 6.98 (s, 1H), 6.86 (bs, 2H), 6.62 (d, J = 8Hz, 1H), 4.46 (t, J = 8Hz, 2H), 3.10 (t, J = 8Hz, 2H), 3.05 (bs, 1 H), 2.81 (bs, 1H), 2.54 (bs, 2H), 2.32 (bs, 2H), 1.77 (m, 1H), 1.90-1.3 (m, 3H), 1.00 (bs, 1 H), 0.50 (bs, 1H); LCMS (APCI+) for C29H32N2O2 m/z 441(M + H)+. |
69.3% | With phosphorus tribromide; In chloroform;Reflux; | Take 9.6g (58.5mmol)Compound 2 obtained in Example 4 is added to a reaction flask,Then add 60g of chloroform,Dropping through a dropping funnel5.8g (21.4mmol)Phosphorus tribromide/20g chloroform solution.After dropping,Heat to reflux for about 5-6 hours.After confirming the reaction,Cool down to 20°C,Add 100g of chloroform;An aqueous solution containing 18 g of sodium carbonate was added dropwise with stirring.Stir and extract thoroughlyResting,Liquid separation,The aqueous phase was extracted with chloroform (100 g×3).Combine the organic phase,Dry with anhydrous sodium sulfatefilter,The filtrate is concentrated,Get an oil,Add methanol, stir to crystallize,Get a solid,12.5g.The resulting solid was dissolved by heating with 25 g of methanol.After completely dissolved,filter,Cool crystallization,Obtained 9.2 g of solid (theoretical amount: 13.28 g);Yield:69.3percent. |
62% | With phosphorus tribromide; In chloroform; for 3h;Heating / reflux; | 5-(2-Bromo-ethyl)-2,3-dihydro-benzofuran: Phosphorus tribromide (0.297 g, 1.097 mmol) was added dropwise to a solution of 2-(2,3-dihydro-benzofuran-5-yl-ethanol (0.500 g, 3.048 mmol) dissolved in chloroform (10 mL) and the mixture was heated at reflux for about 3 hours. The mixture was partitioned between 10percent sodium carbonate and dichloromethane at ambient temperature. Standard extractive workup gave the title compound as an oil which solidified on standing (0.430 g, 62percent). m.p. 60-67° C.; 1H NMR (400 MHz, CDCl3) delta 3.08 (t, J=7.7 Hz, 2H), 3.19 (t, J=8.7 Hz, 2H), 3.52 (t, J=7.7 Hz, 2H), 4.56 (t, J=8.7 Hz, 2H), 6.72 (d, J=8.3 Hz, 1H), 6.94 (d, J=7.9 Hz, 1H), 7.04 (s, 1H); IR (KBr) delta 2960, 2900, 1612, 1491, 1241 cm-1. |
With phosphorus tribromide; In tetrachloromethane; | Preparation 17 Preparation of 5-(2-bromoethyl)-2,3-dihydrobenzofuran phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g - see Preparation 16) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2 x 10 ml). The combined dichloromethane extracts were dried (MgSO4 and concentrated in vacuo to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60-62°c. 1H-N.M.R. (CDCl3delta= 7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With phosphorus tribromide; In tetrachloromethane; | (B) Preparation of 5-(2-bromoethyl)-2,3-dihydrobenzofuran STR77 Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g -- see Part A) in carbon tetrachloride (3 ml) and the mixture heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer extracted with dichloromethane (2*10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60°-62°. 1 H N.M.R. (CDCl3) delta=7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With phosphorus tribromide; | PREPARATION 17 Preparation of 5-(2-bromoethyl)-2,3-dihydrobenzofuran STR31 Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g--see Preparation 16) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2*10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60°-62° C. 1 H-N.M.R. (CDCl3) delta=7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With phosphorus tribromide; | Preparation 6 5-(2-Bromoethyl)-2,3-dihydrobenzofuran STR53 Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g) (see Preparation 5) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate solution (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulphate and evaporated to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60°-62° C. 1 H-NMR (CDCl3) delta=7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With phosphorus tribromide; In tetrachloromethane; | (B) Preparation of 5-(2-bromoethyl)-2,3-dihydrobenzofuran STR38 Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g) in carbon tetrachloride (3 ml) and the mixture heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer extracted with dichloromethane (2*10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60°-62° C. 1 H N.m.r. (CDCl3)delta=7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
PREPARATION 8 5-(2-Bromoethyl)-2,3-dihydrobenzofuran Phosphorus tribomide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g) (Preparation 7) in carbon tetrachloride (3 ml) and the mixture heated under reflux for 3 hours and partitioned between 10percent aqueous sodium carbonate solution (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted with dichloromethane. The combined dichloromethane extracts were dried (MfSO4) and evaporated to give the title compound (0.584 g) as an oil which crystallized on standing, m.p. 60°-62° C., and which was characterised by its 1 H-NMR spectrum. 1 H NMR (CDCl3) delta=7.10(s,1H), 7.00-6.95(d,1H), 6.80-6.70(d,1H), 4.65-4.55(t,2H), 3.60-3.50(t,2H), 3.25-3.15(t,2H) and 3.15-3.10(t,2H). | ||
With phosphorus tribromide; | PREPARATION 9 5-(2-Bromoethyl)-2,3-dihydrobenzofuran STR42 Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g--see Preparation 8) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer Was extracted with dichloromethane (2*10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60°-62° C. 1 H N.m.r. (CDCl3) delta=7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With phosphorus tribromide; | PREPARATION 31 5-(2-Bromoethyl)-2,3-dihydrobenzofuran STR137 Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g--see Preparation 30) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2*10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallized on standing, (0.584 g), m.p. 60°-62° C. 1 H-n.m.r. (CDCl3) delta=7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With phosphorus tribromide; | PREPARATION 13 Preparation of 5-(2-bromoethyl)-2,3-dihydrobenzofuran STR34 Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g --see Preparation 12) in carbon tetrachloride (3 ml) and the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2*10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60°-62° C. 1 H N.m.r. (CDCl3) delta=7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With phosphorus tribromide; | Preparation 20 Preparation of 5-(2-bromoethyl)-2,3-dihydrobenzofuran Phosphorus tribromide (0.37 g) was added to a solution of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran (0.612 g - see Preparation 19) in carbon tetrachloride (3 ml) and the mixture heated under reflux for 3 hours. On cooling to room temperature, the mixture was partitioned between 10percent aqueous sodium carbonate (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous layer extracted with dichloromethane (2 * 10 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallized on standing, yield 0.584 g, m.p. 60-62°. 1H N.M.R. (CDCl3) delta = 7.10 (s, 1H); 7.00-6.95 (d, 1H); 6.80-6.70 (d, 1H); 4.65-4.55 (t, 2H); 3.60-3.50 (t, 2H); 3.25-3.15 (t, 2H); 3.15-3.10 (t, 2H) ppm. | |
With dibromotriphenylphosphorane; In acetonitrile; at 25 - 78℃;Inert atmosphere; | Stage-1 :PREPARATION OF 5-(2-BROMOETHYL)-2,3-DIHYDROBENZOFURAN2- (2,3-Dihydrobenzofuran-5-yl)ethanol (10 g, 0.06 mol) was dissolved in acetonitrile (60 ml) at 25 +/- 2°C under nitrogen atmosphere and triphenylphosphine dibromide (27.02 g, 0.06 mol) was added in one lot at 25 +/- 2°C. The reaction mass was heated to 76-78°C and stirred for 2 h. Reaction progress was monitored by TLC [Ethyl acetate: n-Hexanes; 2:8 v/v], Acetonitrile was completely distilled off under reduced pressure at 76-78°C. The residue was cooled and the product was extracted with n-hexanes (4 x 30 ml) at 25 +/- 2°C. The solution was filtered and diluted with ethyl acetate (50 ml) and washed with 5percent w/w aqueous sodium bicarbonate solution (2 x 50 ml) at 25 +/- 2°C. The organic layer was concentrated under reduced pressure at 40-50°C.Yield: 7 g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | 2-(2,3-Dihydro-benzofuran-5-yl)-ethanol Borane-THF complex (1 M) (52ml_, 52mmol) was slowly added to a solution of 2,3- dihydro-5-benzofuranacetic acid (4.62g, 25.9mmol) in 15OmL dry THF cooled to O0C under a nitrogen atmosphere. The reaction mixture was allowed to warm up to RT and stirred for 2Oh. Water (5OmL) was added, and the mixture stirred for 20 min. Ethyl acetate was added and the phases were separated. The aqueous layer was further extracted with ethyl acetate, the combined organic layers were dried (MgSO4) and concentrated to give the title product as light brown viscous oil. Yield: 4.2g (100%) LC-MS (Method 2): Rt 2.37 mins, molecular ion not observed. | |
89.7% | With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 10℃; for 4.0h;Reflux; | 600 g of tetrahydrofuran was added to the reaction flask.Then add 40g (1.058mol) sodium borohydride,75 g (0.421 mol) of the compound 1 obtained in Example 5 was added with stirring.Insulation does not exceed 10C during the joining process.After the addition,142 g (1.00 mol) of boron trifluoride diethyl ether complex were initially added dropwise.About 2hrs have been added,Keep the temperature within 15 C during the addition.After dropping,Remove ice salt water,Naturally warm to room temperature;Reheat to reflux,After about 2hrs,After the reaction is completed,Cool down to 15C,Methanol 200g was added dropwise.Then add 420g concentrated hydrochloric acid solution,After stirring,Tetrahydrofuran is concentrated under reduced pressureAfter the basic concentration of tetrahydrofuran is complete,An aqueous solution of g containing 35 g of sodium hydroxide is added,Add 900g ethyl acetate extraction,Liquid separation,The aqueous phase is extracted again with 600 g of ethyl acetate.Combine the organic phase,Dry with anhydrous sodium sulfatefilter,Concentrate under reduced pressure,Get an oil,62g (theoretical quantity: 69.12g);Yield:89.7%. |
80.1% | With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 10℃; for 4.0h;Reflux; | 208 g of tetrahydrofuran was added to the reaction flask.Then add 13g (0.344mol) sodium borohydride,Add with stirring26g (0.146mol)Compound 1 obtained in Example 3,Insulation does not exceed 10C during the joining process.After the addition,49 g (0.345 mol) of boron trifluoride diethyl ether complex were initially added dropwise for about 2 hours.After dropping,The temperature of the dropping process does not exceed 15C.After the addition,Remove ice salt water,Naturally warm to room temperature;Reheat to reflux,After about 2hrs,After the reaction is completed,Cool down to 15C,Methanol 60 g was added dropwise.Then add 140g concentrated hydrochloric acid solution,After stirring,Tetrahydrofuran is concentrated under reduced pressureAfter the basic concentration of tetrahydrofuran is complete,An aqueous solution containing 11 g of sodium hydroxide is added,Add 300g ethyl acetate extraction,Liquid separation,The aqueous phase is extracted with 200 g of ethyl acetate.Combine the organic phase,Dry with anhydrous sodium sulfatefilter,Concentrate under reduced pressure,Get an oil,19.2g (theoretical quantity:23.96g);Yield:80.1%. |
62% | Synthesis of (1) was accomplished using the commercially available piperidine-3-ol (8) according to Scheme 1. The dl-mixture of piperidine-3-ol was resolved according to the method described in JCS Perkin Trans Il (1981), 697 using D (+)-10-camphorsulfonic acid and 3R(+) hydroxypiperidine (+)-10-camphorsulfaonate (2) was obtained after recrystallization. (2) was then converted to 3-(1-carbamoyl-1 ,1-diphenylmethyl)piperidine (6) in four steps using the methods described in European Patent (EP 0 376 358 A1). (6) was EPO <DP n="32"/>then allowed to react with (7) (prepared by a known procedure- Dunn et al, in J. Med Chem (1986) 2236) in the presence of potassium carbonate in acetonitrile at reflux to give (8). Compound (8) was used in the antiviral assay after in-house analysis by proton NMR and LCMS. 1 H NMR (400 MHz, DMSO-d6) delta 7.30 (m, 10H), 7.03 (s, 1H)1 6.98 (s, 1H), 6.86 (bs, 2H), 6.62 (d, J = 8Hz, 1H), 4.46 (t, J = 8Hz, 2H), 3.10 (t, J = 8Hz, 2H), 3.05 (bs, 1 H), 2.81 (bs, 1H), 2.54 (bs, 2H), 2.32 (bs, 2H), 1.77 (m, 1H), 1.90-1.3 (m, 3H), 1.00 (bs, 1 H), 0.50 (bs, 1H); LCMS (APCI+) for C29H32N2O2 m/z 441(M + H)+. | |
With lithium aluminium tetrahydride; aqueous sodium hydroxide; In tetrahydrofuran; water; | Preparation 16 Preparation of 5-(2-hydroxyethyl) -2,3-dihydrobenzofuran A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g - see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0C. The mixture was allowed to warm to room temperature and stirred for 1 hour. water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2 x 50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1H-N.M.R. (CDCl3 delta = 7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | (A) Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran STR76 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g -- see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added over 10 minutes, dropwise, to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was then added dropwise with caution followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H N.M.R. (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | EXAMPLE 50 Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran STR64 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g-see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added over 10 minutes, dropwise, to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was then added dropwise with caution followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H N.M.R. (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | PREPARATION 16 Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran STR30 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g--see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H-N.M.R. (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | Preparation 15 5 -(2-Hydroxyethyl)-2,3-dihydrobenzofuran STR49 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g - see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H N.M.R. (CDCl3)delta-7.10 (s, 1H); 7.00 (d, J=8Hz, 1H); 6.75 (m, 1H); 4.55-4.65 (m, 2H); 3.75-3.90 (m, 2H); 3.15-3.30 (m, 2H); 2.80-2.90 (m, 2H); 1.75-1.85 (broad s, 1H). | |
With sodium hydroxide; In tetrahydrofuran; water; | (A) Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran STR37 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g --see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H N.m.r. (CDCl3)delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | Preparation 5 5-(2-Hydroxyethyl)-2,3-dihydrobenzofuran STR52 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g--see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide solution (1.5 ml) and water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate. The filtrate and washings were combined and evaporated to give the title compound as an oil, yield 3.3 g. 1 H-NMR (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | PREPARATION 7 5-(2-Hydroxyethyl)-2,3-dihydrobenzofuran A solution of (2,3-dihydro-5-benzofuranyl)acetic acid (4.9 g--see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide solution (1.5 ml) and water (4.5 ml). The mixture was filtered and the inorganic salts were washed with ethyl acetate. The filtrate and washings were combined and evaporated to give the title compound as an oil, (3.3 g), which was characterised by its 1 H-NMR spectrum. 1 H-NMR (CDCl3) delta=7.10 (s,1H), 7.00 (d, 1H), 6.75(m,1H), 4.65-4.55(m,2H), 3.90-3.75(m,2H), 3.30-3.15(m,2H), 2.90-2.80(m,2H) and 1.85-1.75(brs,1H). | |
With sodium hydroxide; In tetrahydrofuran; water; | PREPARATION 8 5-(2-Hydroxyethyl)-2,3-dihydrobenzofuran STR41 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g--see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide solution (1.5 ml) and water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H-N.m.r. (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | PREPARATION 30 5-(2-Hydroxyethyl)-2,3-dihydrobenzofuran STR136 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g--see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as as oil, (3.3 g). 1 H-n.m.r. (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (broad s, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | PREPARATION 12 Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran STR33 A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g--see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H N.m.r. (CHCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. | |
With sodium hydroxide; In tetrahydrofuran; water; | Preparation 19 Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran A solution of <strong>[69999-16-2](2,3-dihydrobenzofuran-5-yl)acetic acid</strong> (4.9 g - see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added over 10 minutes, dropwise, to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was then added dropwise with caution followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2 * 50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1H N.M.R. (CDCl3) delta = 7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere 2.1: potassium carbonate / acetonitrile / 25 - 70 °C / Inert atmosphere 2.2: 5 - 30 °C / pH 2 - 9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr 2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux |
Tags: 87776-76-9 synthesis path| 87776-76-9 SDS| 87776-76-9 COA| 87776-76-9 purity| 87776-76-9 application| 87776-76-9 NMR| 87776-76-9 COA| 87776-76-9 structure
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