Structure of 5341-95-7
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| CAS No. : | 5341-95-7 |
| Formula : | C4H10O2 |
| M.W : | 90.12 |
| SMILES Code : | C[C@@H](O)[C@@H](O)C |
| English Name : | Meso-2,3-butanediol |
| MDL No. : | MFCD00077669 |
* 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 |
|---|---|---|
| With sulfuric acid diacetate of meso-2.3-butylene glycol; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 67% | With dmap; triethylamine In dichloromethane at 20℃; Sealed tube; | 3. Standard procedures for the preparation of polyol esters General procedure: Triethylamine (1.5 eq. per hydroxyl) and N,N-dimethylaminopyridine (0.0125 eq. per hydroxyl)were added to a solution of polyol alcohol (20 mmol) in DCM (100 mL). Acyl chloride or acidanhydride (1.25 eq. per hydroxyl) was added dropwise to the stirred solution in an ice-water bath.The resulting solution was warmed to room temperature and stirred until TLC analysis showed noremaining starting materials. The reaction mixture was transferred to a separatory funnel and washedsequentially with water (100 mL), 1M HCl aqueous solution (100 mL), and saturated aqueous NaClsolution (100 mL). The organic phase was dried with Na2SO4 and concentrated in vacuo. The crudeproduct was purified by flash column chromatography to afford the corresponding polyol esters (PE :EA = 10 : 1). |
| With sulfuric acid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pyridine diacetate of meso-2.3-butylene glycol; | ||
| With 2,3-Dimethylaniline diacetate of meso-2.3-butylene glycol; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With trichlorophosphate | ||
| With triethylamine; trichlorophosphate In diethyl ether at 0℃; for 0.5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93% | Stage #1: (2R,3S)-2,3-butanediol With thionyl chloride In dichloromethane at 60℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With ruthenium trichloride; sodium periodate In dichloromethane; acetonitrile at 0℃; Inert atmosphere; Schlenk technique; stereoselective reaction; | |
| With sulfuric acid; sulfur trioxide |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | With pyridine 1.) from 10 to 13 deg C, 1 h, 2.) RT, overnight; | |
| With pyridine at 0℃; | ||
| 25.01 g | Stage #1: (2R,3S)-2,3-butanediol With triethylamine In dichloromethane at -78℃; Stage #2: methanesulfonyl chloride In dichloromethane at -78 - 0℃; for 2.3h; | 168.168a 2,3-bis(methanesulfonyloxy)butane Samples of meso-2,3-butanediol (10 g, 111 mmol, Aldrich) and triethylamine (92.8 mL, 666 mmol) were dissolved in methylene chloride. The solution was cooled to -78° C, and methanesulfonyl chloride (25.8 mL, 333 mmol) was added dropwise. A precipitate formed. The mixture was diluted with additional methylene chloride, and the mixture was stirred for 20 minutes at -78° C. and at 0° C. for 2 hours. The reaction mixture was warmed to room temperature, diluted with additional solvent, and washed with H20, aqueous NaHC03 and aqueous NaCl. The organic solution was dried over MgS04, and the solvent was removed to afford the title compound (25.01 g). JH |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | With hydrogen In toluene for 1.91667h; Further byproducts given. Yields of byproduct given; | |
| 50% | With hydrogen In toluene for 1.91667h; Yield given. Further byproducts given. Title compound not separated from byproducts; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | With hydrogen In toluene for 1.91667h; Yield given. Further byproducts given. Title compound not separated from byproducts; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | With pyridinium p-toluenesulfonate In benzene | |
| 99% | With pyridinium p-toluenesulfonate In toluene at 20℃; for 12h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 95% 2: 99% | With pyridinium p-toluenesulfonate In benzene Ambient temperature; | |
| 1: 99% 2: 95% | With pyridinium p-toluenesulfonate In toluene at 20℃; for 12h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 4 A molecular sieve; triethylamine; (S)-1-methyl-2-[(N-benzyl-N-methylamino)methyl]pyrrolidine In dichloromethane at -78℃; for 3h; Yield given. Yields of byproduct given; | ||
| With 4 A molecular sieve; (S)-1-methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine In dichloromethane at -78℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | ||
| With chloro-diphenylphosphine; triethylamine; Cinchonin In tetrahydrofuran at -78℃; for 4h; Title compound not separated from byproducts; |
| With bis[(S)-4-benzyloxazolin-2-yl]-bis[3,5-di(CF3)phenyl]BH; N-ethyl-N,N-diisopropylamine; copper dichloride In dichloromethane at 0 - 20℃; | ||
| With (4R,4’R)-2,2’-(propane-2,2-diyl)bis(4-benzyl-4,5-dihydrooxazole); N-ethyl-N,N-diisopropylamine; copper dichloride In dichloromethane at 0 - 20℃; Title compound not separated from byproducts; | ||
| With chiral diamine-CuCl2; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; Title compound not separated from byproducts; | ||
| With chiral polymer-supported bis(imidazoline)-based ligand; N-ethyl-N,N-diisopropylamine; copper(l) chloride In dichloromethane at -40℃; for 47h; Title compound not separated from byproducts; | ||
| With 2BF4(1-)*C46H36N6O4S2*Cu(2+); N-ethyl-N,N-diisopropylamine In dichloromethane at -40℃; for 64h; optical yield given as %ee; enantioselective reaction; | ||
| 82 % ee | With (8R,8aS,16R,16aS)-8a,16a-bis(3,5-dimethylphenyl)-2,3,10,11-tetramethoxy-5,6,8,8a,13,14,16,16a-octahydro-8,16-epoxypyrazino[2,1-a:5,4-a']diisoquinoline; N-ethyl-N,N-diisopropylamine; copper dichloride In dichloromethane at -78℃; Inert atmosphere; Overall yield = 79 %; stereoselective reaction; | 4.5 General procedure for the asymmetric acylation of meso-1,2-diols catalyzed by CuCl2 complexes with ligands 14 and 15 General procedure: Ligand 14 or 15 (0.016 mmol) and CuCl2 (2.0 mg, 0.015 mmol) were stirred in DCM (2.4 mL) until complete dissolution of copper salt (4-24 h). A green solution of the generated complex was added to a solution of meso-1,2-diol (0.5 mmol) in DCM (4.0 mL) and the mixture was cooled to -78 °C. Next, diisopropylethylamine (170 μL, 1.0 mmol) and benzoyl chloride (0.26 mL, 2.4 mmol) were added. The reaction mixture was stirred until the 1,2-diol was consumed (TLC control), after which the mixture was quenched by the addition of 0.1 M aqueous citric acid. The resulting mixture was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were washed sequentially with 0.1 M aqueous citric acid, water, and brine, dried over anhydrous MgSO4, and the solvent was removed in vacuo. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1-7:3) to give the desired monobenzoate. |
| 88 % ee | With C24H28N2O; N-ethyl-N,N-diisopropylamine; copper dichloride In dichloromethane at -78℃; for 24h; Overall yield = 74 %; enantioselective reaction; | |
| 30 % ee | With C50H44N4O6Zn2; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 12h; Inert atmosphere; Overall yield = 90 %; enantioselective reaction; | |
| 40 % ee | Stage #1: (2R,3S)-2,3-butanediol With C58H38N4O2(2-)*2Zn(2+)*2C2H3O2(1-); N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere; Stage #2: benzoyl chloride In dichloromethane at 0℃; for 8h; Inert atmosphere; Overall yield = 96 %; enantioselective reaction; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With pyridine In dichloromethane at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 96% | With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | With toluene-4-sulfonic acid In toluene at 20℃; for 24h; |