| 83.1% |
With sodium tetrahydridoborate In tetrahydrofuran at 20℃; Cooling with ice; |
1 Example 1: Preparation of 3- (1-hydroxy) ethylphenol (IIIa)
150.00 g (1.10 mol) of 3-hydroxyacetophenone compound (corresponding to R3 in formula II is methyl) are dissolved in 500 ml of tetrahydrofuran,51.00 g (1.30 mol) of sodium borohydride are added portionwise in an ice bath, Stirring was carried out at room temperature and the progress of the reaction monitored by TLC.After the reaction was completed, tetrahydrofuran was removed by rotary evaporation, Add ice-water quenching sodium borohydride, dilute hydrochloric acid was added dropwise to a pH of 5-6.The aqueous layer was extracted three times with ethyl acetate, the mixed ethyl acetate layer was dried over anhydrous sodium sulfate,After concentration and evaporated to give a pale yellow solid IIIa, yield 83.1%. |
| 78% |
With methanol; sodium tetrahydridoborate at 20℃; for 2h; |
15.A Step A:
Step A: To a solution of 3 -hydroxy acetophenone (2.72 g, 20 mmol) in MeOH (lOmL) was added sodium borohydride (380 mg, 10 mmol). After stirring at room temperature for 2 h, the reaction mixture was acidified to pH <7 with aqueous HC1 (1 N). MeOH was removed by rotoevaporation under reduced pressure. The mixture was partitioned in water and EtO Ac. The organic layer was washed with water, dried over MgS04, filtered and concentrated under reduced pressure to provide 3 -(1 -hydroxy ethyl)phenol (2.15 g, 78%). MS m/z 137.1 [M-H]~. |
| 78% |
With methanol; sodium tetrahydridoborate at 20℃; for 2h; |
15.A
Step A: To a solution of 3-hydroxyacetophenone (2.72 g, 20 mmol) in MeOH (10 mL) was added sodium borohydride (380 mg, 10 mmol). After stirring at room temperature for 2 h, the reaction mixture was acidified to pH<7 with aqueous HCl (1 N). MeOH was removed by rotoevaporation under reduced pressure. The mixture was partitioned in water and EtOAc. The organic layer was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure to provide 3-(1-hydroxyethyl)phenol (2.15 g, 78%). MS m/z 137.1 [M-H]-. |
| 71% |
With [Ru(P(Ph){(o-C6H4)(1,2,3-N3C(Ph)CH)}2)(Cl)(PPh3)(H2O)]Cl; isopropanol; potassium hydroxide at 80℃; for 3h; Inert atmosphere; |
|
| 33% |
With (2-((dimethylamino)methyl)phenyl)dimethyltin; phenylsilane In tetrahydrofuran at 20℃; for 12h; |
|
| 100 % Spectr. |
With hydrogenchloride; sodium cyanotrihydridoborate In methanol for 24h; |
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With sodium tetrahydridoborate In methanol at 0 - 5℃; |
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With sodium tetrahydridoborate In lithium hydroxide monohydrate |
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With Candida tenuis AKR2B5 xylose reductase [E.(1)C11175]; lithium hydroxide monohydrate; nicotinamide adenine dinucleotide In ethanol at 25℃; aq. phosphate buffer; Enzymatic reaction; |
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With sodium tetrahydridoborate In methanol at 0 - 20℃; |
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With sodium tetrahydridoborate In ethanol for 1h; |
Synthesis of racemic alcohols
General procedure: The racemic alcohols were prepared by the reduction of the corresponding ketones with sodium borohydride (0.5mL equivalent) in ethanol (5mL per mmol of ketone) over 1h. The reaction was quenched by adding a 10% (v/v) hydrochloric acid solution, after which the solvent was evaporated in vacuum, the mixture extracted with ethyl acetate (3 times) and the product concentrated in vacuum. Pd/C was added (10%, w/w, 27mg) to a solution of 2e (207mg, 1.50mmol) in ethyl acetate (10mL) and the mixture was stirred under a hydrogen atmosphere pressurized reactor at room temperature for 12h. The catalyst was filtered through Celite and the filtrate was concentrated in vacuum followed by purification with silica gel chromatography using hexane/ethyl acetate as the mobile phase to produce rac-1e |
| 99 %Chromat. |
With hydrogen In lithium hydroxide monohydrate at 20℃; for 3h; Green chemistry; chemoselective reaction; |
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With C62H62Cl4N2O4P4Ru2*C6H15N; potassium carbonate; isopropanol at 82℃; Schlenk technique; Inert atmosphere; |
General Procedure for Transfer Hydrogenation
General procedure: An acetophenone derivative (1 mmol), 2-propanol (2 mL), catalyst (0.1 mmol%), K2CO3 (5 mmol %) were introduced into a Schlenk tube under argon. The resulting solution was heated at 82 °C for 12 h. The solvent was then removed under reduced pressure and purified by flash chromatography (hexane-EtOAc, 10:1). Product distribution was determined by GC yield of the corresponding alcohol. |
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With β-D-glucopyranose; NADP In aq. phosphate buffer at 37℃; Flow reactor; |
3.6.2. Substrates 2; 3: 4-phenyl-2-butanone; 3'-hydroxyacetophenone
General procedure: 4-Phenyl-2-butanone and 3'-hydroxyacetophenone were used as bulky ketones for the KREDbiotransformations. The GDH regeneration system (Scheme 2) was used to regenerate NADP+.The reaction mixture contained 0.1 M potassium phosphate buer (pH 6.5), 20 mM (50 and 100 mM) of4-phenyl-2-butanone or 30-hydroxyacetophenone, 100 mM glucose (200 and 400 mM), and 250 μMNADP+. The reaction mixture recirculates through a column reactor (1 mL) according to the Scheme 1.Reactions were carried out in a tempered reactor in a total volume of 10 mL at 37 °C with mixing(250 rpm). |
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Multi-step reaction with 2 steps
1: Fe(CH<SUB>2</SUB>SiMe<SUB>3</SUB>)<SUB>2</SUB>(pyridine)<SUB>2</SUB> / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere; Glovebox
2: potassium carbonate / methanol / 0.5 h / 25 °C / Inert atmosphere |
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With methanol; sodium tetrahydridoborate at 30℃; |
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With potassium-t-butoxide; [Ru(6,6'-bis(aminomethyl)-2,2'-bipyridine)Cl2]; isopropanol at 80℃; for 16h; Inert atmosphere; Sealed tube; |
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