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Chemical Structure| 58917-25-2 Chemical Structure| 58917-25-2
Chemical Structure| 58917-25-2

(R)-γ-Valerolactone

CAS No.: 58917-25-2

4.5 *For Research Use Only !

Cat. No.: A344743 Purity: 97%

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Product Details of [ 58917-25-2 ]

CAS No. :58917-25-2
Formula : C5H8O2
M.W : 100.12
SMILES Code : O=C1O[C@H](C)CC1
MDL No. :MFCD01863131
InChI Key :GAEKPEKOJKCEMS-SCSAIBSYSA-N
Pubchem ID :642783

Safety of [ 58917-25-2 ]

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 [ 58917-25-2 ]

* 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 [ 58917-25-2 ]

[ 58917-25-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 58917-25-2 ]
  • [ 62327-21-3 ]
  • [ 1073630-51-9 ]
  • (2Z,6R)-6-hydroxyhept-2-enoic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Solution A: suspend 10.71 g (267.7 mmol) of 60percent sodium hydride in 150 ml abs. THF and add dropwise, with cooling, 43.3 ml (276.7 mmol) P,P-dimethylphosphonoacetic acid tert.-butyl ester. Stir the mixture at RT, obtaining a solution after approx. 30 min. Add 187.4 ml (187.4 mmol) of a 1 M solution of D113AH in THF dropwise to a solution of 17.87 g (178.5 mmol) (R)-gamma-valerolactone [(5R)-5-methyldihydrofuran-2(3H)-one] in 200 ml abs. THF cooled to -78° C. Stir the solution for a further 1 h at -78° C. and then add solution A prepared above. At the end of addition, slowly heat the mixture to RT and stir overnight at RT. Add the reaction mixture to 300 ml ethyl acetate and precipitate with 50 ml concentrated potassium sodium tartrate solution. After phase separation, extract the aqueous phase again with ethyl acetate. Combine the organic phases, wash with satd. sodium chloride solution, dry over magnesium sulphate and concentrate under vacuum. Purify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1). 32.2 g (90.1percent of theor.) of the target product, containing small amounts of the cis-isomer, is obtained. MS (DCI): m/z=218 (M+NH4)+ 1H-NMR (400 MHz, DMSO-d6): delta=6.70 (dt, 1H), 5.73 (d, 1H), 4.44 (d, 1H), 3.58 (m, 1H), 2.28-2.13 (m, 2H), 1.47-1.40 (m, 2H), 1.45 (s, 9H), 1.04 (d, 3H).
  • 2
  • [ 58917-25-2 ]
  • [ 62327-21-3 ]
  • [ 1073630-51-9 ]
YieldReaction ConditionsOperation in experiment
Solution A: 10.71 g (267.7 mmol) of 60percent sodium hydride are suspended in 150 ml of abs. THF, and 43.3 ml (276.7 mmol) of tert-butyl P,P-dimethylphosphonoacetate are added dropwise with cooling. The mixture is stirred at RT, and after about 30 min a solution is formed.187.4 ml (187.4 mmol) of a 1 M solution of DIBAH in THF are added dropwise to a solution, cooled to -78° C., of 17.87 g (178.5 mmol) of (R)-gamma-valerolactone [(5R)-5-methyldihydrofuran-2(3H)-one] in 200 ml of abs. THF. The solution is stirred at -78° C. for 1 h, and solution A, prepared above, is then added. After the end of the addition, the mixture is slowly warmed to RT and stirred at RT overnight. The reaction mixture is added to 300 ml of ethyl acetate and extracted by stirring with 50 ml of concentrated potassium sodium tartrate solution. After phase separation, the aqueous phase is re-extracted with ethyl acetate. The organic phases are combined, washed with sat. sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 5:1). This gives 32.2 g (90.1percent of theory) of the target product which contains small amount of the cis-isomer.MS (DCI): m/z=218 (M+NH4)+ 1H-NMR (400 MHz, DMSO-d6): delta=6.70 (dt, 1H), 5.73 (d, 1H), 4.44 (d, 1H), 3.58 (m, 1H), 2.28-2.13 (m, 2H), 1.47-1.40 (m, 2H), 1.45 (s, 9H), 1.04 (d, 3H).
Example 5A tert-Butyl (2E,6R)-6-hydroxyhept-2-enoate Solution A: 10.71 g (267.7 mmol) of 60percent pure sodium hydride were suspended in 150 ml of abs. THF, and 43.3 ml (276.7 mmol) of tert-butyl P,P-dimethylphosphonoacetate were added dropwise with cooling. The mixture was stirred at RT, and after about 30 min a solution had formed. 187.4 ml (187.4 mmol) of a 1 M solution of DIBAH in THF were added dropwise to a solution, cooled to -78° C., of 17.87 g (178.5 mmol) of (R)-gamma-valerolactone [(5R)-5-methyl-dihydrofuran-2(3H)-one] in 200 ml of abs. THF. The solution was stirred at -78° C. for 1 h, and solution A, prepared above, was then added. After the addition had ended, the mixture was slowly warmed to RT and stirred at RT overnight. The reaction mixture was then added to 300 ml of ethyl acetate and extracted with 50 ml of concentrated potassium sodium tartrate solution. After phase separation, the aqueous phase was reextracted with ethyl acetate. The organic phases were combined, washed with sat. sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). This gave 32.2 g (90.1percent of theory) of the target product, which contained small amounts of the cis-isomer. MS (DCI): m/z=218 (M+NH4)+ 1H-NMR (400 MHz, DMSO-d6): delta=6.70 (dt, 1H), 5.73 (d, 1H), 4.44 (d, 1H), 3.58 (m, 1H), 2.28-2.13 (m, 2H), 1.47-1.40 (m, 2H), 1.45 (s, 9H), 1.04 (d, 3H).
Example 1Atert-Butyl (2E,6R)-6-hydroxyhept-2-enoate Solution A: 10.71 g (267.7 mmol) of 60percent sodium hydride are suspended in 150 ml of abs. THF, and 43.3 ml (276.7 mmol) of tert-butyl P,P-dimethylphosphonoacetate are added dropwise with cooling. The mixture is stirred at RT, and after about 30 min a solution is formed.187.4 ml (187.4 mmol) of a 1 M solution of DIBAH in THF are added dropwise to a solution, cooled to -78° C., of 17.87 g (178.5 mmol) of (R)-gamma-valerolactone [(5R)-5-methyldihydrofuran-2(3H)-one] in 200 ml of abs. THF. The solution is stirred at -78° C. for 1 h, and solution A, prepared above, is then added. After the end of the addition, the mixture is slowly warmed to RT and stirred at RT overnight. The reaction mixture is added to 300 ml of ethyl acetate and extracted by stirring with 50 ml of concentrated potassium sodium tartrate solution. After phase separation, the aqueous phase is re-extracted with ethyl acetate. The organic phases are combined, washed with sat. sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). This gives 32.2 g (90.1percent of theory) of the target product which contains small amounts of the cis-isomer.MS (DCI): m/z=218 (M+NH4)+ 1H-NMR (400 MHz, DMSO-d6): delta=6.70 (dt, 1H), 5.73 (d, 1H), 4.44 (d, 1H), 3.58 (m, 1H), 2.28-2.13 (m, 2H), 1.47-1.40 (m, 2H), 1.45 (s, 9H), 1.04 (d, 3H).
Example 10Atert-butyl (2E,6R)-6-hydroxyhept-2-enoateSolution A: 10.71 g (267.7 mmol) of 60percent sodium hydride are suspended in 150 ml of abs. THF, and 43.3 ml (276.7 mmol) of tert-butyl P,P-dimethylphosphonoacetate are added dropwise with cooling.The mixture is stirred at RT, and after about 30 min a solution is formed.187.4 ml (187.4 mmol) of a 1 M solution of DIBAH in THF are added dropwise to a solution, cooled to -78° C., of 17.87 g (178.5 mmol) of (R)-gamma-valerolactone [(5R)-5-methyl-dihydrofuran-2(3H)-one] in 200 ml of abs. THF.The solution is stirred at -78° C. for 1 h, and solution A prepared above is then added.After the addition, the mixture is slowly warmed to RT and stirred at RT overnight.The reaction mixture is added to 300 ml of ethyl acetate and extracted with 50 ml of concentrated potassium sodium tartrate solution.After phase separation, the aqueous phase is reextracted with ethyl acetate.The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure.The residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1).This gives 32.2 g (90.1percent of theory) of the target product which contains small amounts of the cis isomer.MS (DCI): m/z=218 (M+NH4)+1H-NMR (400 MHz, DMSO-d6): delta=6.70 (dt, 1H), 5.73 (d, 1H), 4.44 (d, 1H), 3.58 (m, 1H), 2.28-2.13 (m, 2H), 1.47-1.40 (m, 2H), 1.45 (s, 9H), 1.04 (d, 3H).

 

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