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Chemical Structure| 185-61-5 Chemical Structure| 185-61-5

Structure of 185-61-5

Chemical Structure| 185-61-5

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Product Details of [ 185-61-5 ]

CAS No. :185-61-5
Formula : C5H8O2
M.W : 100.12
SMILES Code : O1CC12COCC2
MDL No. :MFCD18333951
InChI Key :SNVWCQVCIGRDCF-UHFFFAOYSA-N
Pubchem ID :63333521

Safety of [ 185-61-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P210-P240-P241-P242-P243-P261-P264-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 185-61-5 ]

* 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.

  • Downstream synthetic route of [ 185-61-5 ]

[ 185-61-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 22929-52-8 ]
  • [ 2181-42-2 ]
  • [ 185-61-5 ]
YieldReaction ConditionsOperation in experiment
1% Step 1. Synthesis of Intermediate 5-2. To a mixture of trimethylsulfoxonium iodide (28.3 g, 139 mmol) in DMSO (60 mL) was added NaH (5.55 g, 60percent in mineral oil, 139 mmol) in portions at 5 °C under N2 and the mixture was stirred at 5 °C for 30 mins. Dihydrofuran-3(2H)- one (10 g, 116 mmol) in DMSO (40 mL) was added dropwise while maintaining the temperature below 15 °C and the resulting mixture was stirred at 15 °C for 20 hrs. The reaction was quenched at 10 °C with water (200 mL) and extracted with MTBE (2 x 200 mL). The combined organic phases were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated and the residue was purified by silica gel chromatography (0percent~40percent EtOAc in PE) to afford Intermediate 5-2 (100 mg, 1percent) as a colorless oil. (0326) 1H NMR (400 MHz, CDCl3) delta 4.12-3.93 (m, 3H), 3.68 (d, J = 10.4Hz, 1H), 3.05 (d, J = 4.4Hz, 1H), 2.96 (d, J = 4.4Hz, 1H), 2.37-2.25 (m, 1H), 2.02-1.92 (m, 1H).
  • 2
  • [ 22929-52-8 ]
  • [ 1774-47-6 ]
  • [ 185-61-5 ]
YieldReaction ConditionsOperation in experiment
13% To a mixture of trimethylsulfoxonium iodide (30.6 g, 150 mmol) in THF (100 mL) was added NaH (5.98 g, 60percent in miniral oil, 150 mmol) in portions at 0°C under N2. The mixture was stirred at 0°C for 30 mins. Dihydrofuran-3(2H)-one (10 g, 116 mmol) in DMSO (100 mL) was added dropwise at 0°C. The reaction mixture was stirred at 0°C for 2 hours. The mixture was poured into ice-water (500 mL) in portions, extracted with DCM (2 x 500 mL). The combined organic phase was washed with brine (500 mL), dried over Na2S04, filtered and concentrated at 30°C. The residue was purified by Combi-flash (EtOAc in PE, 0percent~40percent) to afford J-l (1.5 g, 13 percent) as an oil. 1H NMR (400 MHz, CDC13) delta 4.11-3.90 (m, 3H), 3.66 (d, / = 10.0 Hz, 1H), 3.03 (d, / = 4.4 Hz, 1H), 2.94 (d, / = 4.0 Hz, 1H), 2.34-2.23 (m, 1H), 2.00-1.88 (m, 1H).
  • 3
  • [ 22929-52-8 ]
  • [ 1030268-24-6 ]
  • [ 185-61-5 ]
YieldReaction ConditionsOperation in experiment
[00534] Compound t-BuOK (782.0 mg, 6.9 mmol, 1.2 eq) were added in DMSO (10.0 mL) and the mixture cooled to around 20 C with stirring. 151-2 (1.3 g, 5.8 mmol, 1.0 eq) was added in portions over a period of 15 min, maintaining the reaction temperature between 20 - 25 C. On completion of the addition, the mixture was maintained at this temperature until a yellow solution was obtained (1 h). DME (2.0 mL) was added to the reaction flask and the solution cooled to 0 - 5 C. A pre-cooled solution of 151-1 (500.0 mg, 5.8 mmol, 1.0 eq) in a mixture of DME (2.0 mL) and DMSO (1.0 mL) was transferred into the reaction mixture over a period of around 45 min, maintaining the reaction temperature between 0 - 5 C. On completion of the addition, the reaction mixture was held at this temperature for a further 1 h. TLC (Petroleum ether : ethyl acetate=10/l) showed no new spots. The product was directly used as a solution in DMSO without further purification. 151-3 (500.0 mg, 5.0 mmol, 85.9percent yield) was obtained in DMSO (11.0 mL).
 

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