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[ CAS No. 171230-81-2 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 171230-81-2
Chemical Structure| 171230-81-2
Structure of 171230-81-2 *Storage: {[proInfo.prStorage]}

Quality Control of [ 171230-81-2 ]

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Product Details of [ 171230-81-2 ]

CAS No. :171230-81-2MDL No. :MFCD28402584
Formula : C10H22O3Si Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :218.37Pubchem ID :10856967
Synonyms :

Computed Properties of [ 171230-81-2 ]

TPSA : 35.5 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.90 Rotatable Bond Count : 5

Safety of [ 171230-81-2 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 171230-81-2 ]

  • Upstream synthesis route of [ 171230-81-2 ]

[ 171230-81-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 17392-83-5 ]
  • [ 18162-48-6 ]
  • [ 171230-81-2 ]
YieldReaction ConditionsOperation in experiment
100% With 1H-imidazole In dichloromethane at 20℃; for 2.00 h; A mixture of methyl noate (5.1 g, 48.99 mmol), (1226) dichloromethane (50 mL), imidazole (5 g, 75 mmol) and tert-butyldimethylsilyl chloride (8.85 g) was stirred for two hours at room temperature. The mixture was diluted with water and extracted three times with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The resulting residue was purified by MPLC eluting with 5percent ethyl acetate in petroleum ether to afford methyl (R)-2-((tert-butyldimethylsilyl)oxy)propanoate (10.67 g, 100percent) as a colorless oil.
93% With 1H-imidazole In dichloromethane at 0 - 20℃; for 6.00 h; To a solution of methyl (R)-2-hydroxylpropanoate 12 (2 g, 19.21 mmol) in dry DCM (60 mL) was added imidazole (1.96 g, 28.815 mmol), and the mixture was stirred for 10 min at 0 °C. To this solution tert-butyldimethylsilyl chloride (3.47 g, 23.05 mmol) was added at 0 °C and the mixture was stirred at room temperature for 6 h. After completion of the reaction, the mixture was diluted with cold water and extracted into DCM (3 .x. 75 mL). The combined extract was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography using hexane/ethyl acetate (97:3) to give pure 13 (3.9 g, 93percent) as a colorless oil. (c 2.8, CHCl3) [Lit.15b +27.2 (c 1.89, CCl4)]; IR (neat, cm-1): νmax 2944, 2894, 2859, 1753, 1255, 1146, 838, 778; 1H NMR (300 MHz, CDCl3): δ 4.25 (q, J = 6.8 Hz, 1H), 3.67 (s, 3H), 1.35 (d, J = 6.8 Hz, 3H), 0.87 (s, 9H), 0.04 (d, J = 7.7 Hz, 6H); 13C NMR (75 MHz, CDCl3): δ 172.6, 67.5, 50.6, 25.0, 20.5, 17.5, -5.6, -6.0; ESI/MS (m/z): 241 (M+Na+).
85% With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18.00 h; Inert atmosphere To a solution of (R)-(+)-methyl lactate (2.95 g, 28.34 mmol) in DMF (20 mL) was added tert-butyldimethyl silyl chloride (6.41 g, 42.51 mmol) and imidazole (6.75 g, 99.18 mmol). After stirring at a room temperature for 18 hr, the reaction mixture was diluted with a saturated aqueous NaCl solution (90 mL) and extracted with petroleum ether (3.x.60 mL). The organic layer was washed with a cold 3percent HCl solution (30 mL) and a saturated aqueous NaCl solution (30 mL), dried over Na2SO4 and concentrated. The remaining residue was purified by silica gel (105 g) with petroleum ether (300 mL), followed by 3percent ethyl acetate in petroleum ether (600 mL). The 3percent ethyl acetate in the petroleum ether fractions was collected and the solvent was removed to give 5.26 g of (R)-(+)-Methyl 2-(tert-butyldimethylsilyloxy)propanoate as colorless oil (85percent yield). 1H NMR (CDCl3): δ 4.26 (q, 1H, J=6.8 Hz, -CH), 3.65 (s, 3H, -OCH3), 1.32 (d, 3H, J=6.8 Hz, -CH3), 0.83 (s, 9H, Si-(CH3)3), 0.03 (s, 3H, Si-CH3), 0.00 (s, 3H, Si-CH3).
67% With 1H-imidazole In dichloromethane at 0 - 20℃; for 2.00 h; Step la: methyl (2R)-2-[(tert-butyIdimethyIsiIyl)oxy]propanoate: into a 250-mL round-bottom flask, was placed a solution of methyl (2R)-2-hydroxypropanoate (5 g, 48.03 mmol, 1 .00 equiv) and Imidazole (6.5 g, 95.59 mmol, 2.00 equiv) in dichloromethane (100 mL). This was followed by the addition of a solution of tert-butyl(chloro)dimethylsilane (8.7 g, 57.72 mmol, 1.20 equiv) in dichloromethane (50 mL) dropwise with stirring at 0 °C. The resulting solution was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of 100 mL of water/ice. The resulting solution was extracted with dichloromethane (3x100 mL) and the organic layers combined. The resulting mixture was washed with brine (3x50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 7 g (67percent) of methyl (2R)-2-[(tert-butyldimethylsilyl)oxy]propanoate as colorless oil.
67% With 1H-imidazole In dichloromethane at 0 - 20℃; for 2.00 h; into a 250-mL round-bottom flask was placed a solution of methyl (2/?)-2-hydroxypropanoate (5 g, 48.03 mmol, 1.00 eq.) and imidazole (6.5 g, 95.59 mmol, 2.00 eq.) in dichloromethane (100 mL), followed by the dropwise addition of a solution of tert-butyl(chloro)dimethylsilane (8.7 g, 57.72 mmol, 1.20 eq.) in dichloromethane (50 mL) at 0 °C. The resulting solution was stirred for 2 h at room temperature. The reaction was quenched by the addition of 100 mL of water/ice. The resulting solution was extracted with dichloromethane (3 x 100 mL) and the organic layers combined. The resulting mixture was washed with brine (3 x 50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford 7 g (67percent) of methyl (2R)- 2-[(tert-butyldimethylsilyl)oxy]propanoate as a colorless oil
67% With 1H-imidazole In dichloromethane at 0 - 20℃; for 2.00 h; into a 250-mL round-bottom flask, was placed a solution of methyl (2R)-2-hydroxypropanoate (5 g, 48.03mmol, 1.00 equiv) and Imidazole (6.5 g, 95.59 mmol, 2.00 equiv) in dichloromethane (100 mL). This was followed by the addition of a solution of tert-butyl(chloro)dimethylsilane (8.7 g, 57.72 mmol, 1.20 equiv) in dichloromethane (50 mL) dropwise with stirring at 0 °C. The resulting solution was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of 100 mL of water/ice. The resulting solution was extracted withdichloromethane (3x100 mL) and the organic layers combined. The resulting mixture waswashed with brine (3x50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 7 g (67percent) of methyl (2R)-2-[(tert-butyldimethylsilyl)oxy]propanoate as colorless oil.
67% With 1H-imidazole In dichloromethane at 0 - 20℃; for 2.00 h; into a 250-mL round-bottom flask, was placed a solution of methyl (2R)-2-hydroxypropanoate (5 g, 48.03mmol, 1.00 equiv) and imidazole (6.5 g, 95.59 mmol, 2.00 equiv) in dichloromethane (100 mL). This was followed by the addition of a solution of tert-butyl(chloro)dimethylsilane (8.7 g, 57.72 mmol, 1.20 equiv) in dichloromethane (50 mL) dropwise with stirring at 0 °C. The resulting solution was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of 100 mL of water/ice. The resulting solution was extracted with dichloromethane (3 x 100 mL) and the organic layers combined. The resulting mixture was washed with brine (3 x 50 mL), dried over anhydrous sodium sulfate and concentrated undervacuum to give 7 g (67percent) of methyl (2R)-2-[(tert-butyldimethylsilyl)oxyjpropanoate as colorless oil.
67% With 1H-imidazole In dichloromethane at 0 - 20℃; for 2.00 h; into a 250-mLround-bottom flask was placed a solution of methyl (2R)-2-hydroxypropanoate (5 g, 48.03mmol, 1.00 eq.) and imidazole (6.5 g, 95.59 mmol, 2.00 eq.) in dichloromethane (100 mL), followed by the dropwise addition of a solution of tert-butyl(chloro)dimethylsilane (8.7 g, 57.72 mmol, 1.20 eq.) in dichloromethane (50 mL) at 0 °C. The resulting solution was stirred for 2 h at room temperature. The reaction was quenched by the addition of 100 mL ofwater/ice. The resulting solution was extracted with dichloromethane (3 x 100 mL) and the organic layers combined. The resulting mixture was washed with brine (3 x 50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford 7 g (67percent) of methyl (2R)- 2-[(tert-butyldimethylsilyl)oxyjpropanoate as a colorless oil.

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