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[ CAS No. 32082-74-9 ] {[proInfo.proName]}

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Chemical Structure| 32082-74-9
Chemical Structure| 32082-74-9
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Product Details of [ 32082-74-9 ]

CAS No. :32082-74-9 MDL No. :MFCD12827426
Formula : C4H6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 86.09 Pubchem ID :-
Synonyms :

Safety of [ 32082-74-9 ]

Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

Application In Synthesis of [ 32082-74-9 ]

* 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 [ 32082-74-9 ]

[ 32082-74-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 24966-39-0 ]
  • [ 32082-74-9 ]
  • [ 141079-89-2 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide In water; isopropyl alcohol 1.) 0 deg C, 10 min, 2.) rt, 2 h;
  • 2
  • [ 37586-57-5 ]
  • [ 32082-74-9 ]
  • [ 18951-85-4 ]
YieldReaction ConditionsOperation in experiment
90% In tetrahydrofuran at -10 - -5℃; for 3h;
  • 3
  • [ 617-48-1 ]
  • [ 636-61-3 ]
  • [ 32082-74-9 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride; sodium borohydrid; lithium chloride; In tetrahydrofuran; methanol; EXAMPLE 2 Direct Reduction of Malic Acid to Lactone (R)-Isomer <strong>[636-61-3]D-Malic acid</strong> (1 gram, 0.0075 moles) was refluxed for 3 hours with 10 ml of anhydrous methanol containing 1% hydrogen chloride to form the dimethyl ester (Scheme II). The solution was concentrated to a syrup and dissolved in 4 ml of tetrahydrofuran. Anhydrous lithium chloride (0.6 grams. 0.014 moles) was added followed by sodium borohydride (0.32 grams, 0.0084 moles) and methanol (2 ml) to provide the reducing agent. The mixture was stirred at room temperature(25 C.) for 6 hours, filtered, concentrated to dryness, treated with methanol (10 ml) containing hydrochloric acid (1 ml) and concentrated to dryness on a rotary evaporator at a bath temperature of 35 C. A further 10 ml of methanol was added and the solution concentrated again. The process was repeated twice again and the final syrup partitioned between ethyl acetate and water 0.4 ml: 8 ml. The ethyl acetate layer was recovered, dried and concentrated to yield (R)-3-hydroxybutyrolactone (0.6 grams, 88%).
  • 4
  • [ 3068-88-0 ]
  • [ 6531-13-1 ]
  • [ 6531-13-1 ]
  • (R)-1-(4-nitrophenyl)ethyl-(S)-3-hydroxybutanoate [ No CAS ]
  • [ 32082-74-9 ]
  • [ 6531-13-1 ]
  • 5
  • [ 3068-88-0 ]
  • [ 6168-83-8 ]
  • [ 32082-74-9 ]
YieldReaction ConditionsOperation in experiment
19 g; 23 g With Candida antarctica Lipase B immobilized on Immobead 150; water; In tert-butyl methyl ether; at 20℃;Enzymatic reaction;Kinetics; Racemic beta-butryrolactone (50 g, 0.58 mol) was dissolved in MTBE(3 L) in a 5 L round-bottomed flask charged with a stir bar. Water (6.3 g,0.35 mol) was added, followed by immobilized CAL-B (3.5 g, 7000 U).The reaction mixture was capped and stirred at room temperature.Aliquots (150 muL) were removed at indicated times and added to 1.0 mLof methanol for chiral GC?MS analysis. After complete conversion of(S)-beta-butyrolactone, the beads were filtered, washed with MTBE, andthe solvent volume reduced to 1 L by rotary evaporation. The reaction mixture was extracted with 400 mL of saturated sodium bicarbonate.The organic phase was dried over anhydrous sodium sulfate which wasthen filtered and washed with MTBE. The solvent was removed by rotary evaporation to yield (R)-beta-butyrolactone as a clear oil (23 g, 92percent).Both the CAL-B and MTBE from this step can be recovered and reused.1H NMR: (400 MHz, CDCl3): delta=4.64?4.72 (m, 1H), 3.55 (ddd,J=16.0, 6.0, 1.4 Hz, 2H) 3.05 (ddd, J=16.5, 4.2, 1.4 Hz, 2H) 1H),1.56 dd J=6.1 Hz, 1.8 Hz, 3H).13C NMR: (100 MHz, CDCl3): delta=168.2, 68.0, 44.4, 20.8 Hz.The aqueous phase was carefully acidified to pH 2 with conc. HCland subjected to continuous liquid-liquid extraction with 500 mL diethylether for 18 h. The ether layer was dried with magnesium sulfate,filtered, and the solvent removed by rotary evaporation to yield (S)-3-hydroxybutyric acid as a clear oil (19 g, 63percent).1H NMR: (400 MHz, CDCl3): delta=4.19?4.27 (m, 1H), 2.44?2.58 (m,2H), 1.25 (d, J=6.4 Hz, 3H)13C NMR: (100 MHz, CDCl3): delta=177.69, 64.39, 42.57, 22.46
  • 6
  • [ 32082-74-9 ]
  • [ 6290-03-5 ]
YieldReaction ConditionsOperation in experiment
79% With sodium tetrahydroborate; In ethanol; at 20℃; (R)-beta-Butryrolactone (18.1 g, 210 mmol) was dissolved in 100% ethanol (100 mL) in an Erlenmeyer flask and cooled in an ice bath.Sodium borohydride (17 g, 450 mmol) was added in small portions over30 min with stirring and allowed to warm to room temperature overnight.The reaction was quenched by dropwise addition of 10% HCl until effervescence ceased and the solvent removed by rotary evaporation.The residue was taken up in 200 mL 25% aqueous K2HPO4 and extracted twice with 250 mL isopropanol. The isopropanol layers were combined and solvent was removed by rotary evaporation to yield a cloudy oil. The material was suspended in dichloromethane, dried over anhydrous sodium sulfate, filtered, and the solvent removed by rotary evaporation to yield (R)-1,3 butanediol as a clear oil. (15.2 g,79%).1H NMR (400 MHz, CDCl3): delta=4.02-4.12 (m, 1H), 3.84-3.92 (m,1H), 3.75-3.83 (m, 1H), 1.64-1.74 (m, 2H), 1.20-1.25 (d,J=6.4 Hz, 3H).13C NMR: (100 MHz, CDCl3): delta=68.30, 61.59, 39.96, 23.81.
  • 7
  • [ 64-17-5 ]
  • [ 32082-74-9 ]
  • [ 24915-95-5 ]
YieldReaction ConditionsOperation in experiment
66% With sulfuric acid at 20℃; 4.2. (R)-Ethyl-3-hydroxybutyrate (R)-β-Butryrolactone (20 g, 230 mmol) was dissolved in 500 mLethanol with 1.0 mL H2SO4 and stirred at room temperature. Aliquots(100 μL) were added to 1.0 mL of methanol and analyzed by GC-MS for conversion of the lactone. Upon completion (> 48 h), a small amount of solid sodium bicarbonate was added and the solvent removed by rotary evaporation. The residue was taken up in dichloromethane and washed with water. The water layer was extracted twice with ethyl acetate. The pooled organic layers were dried with magnesium sulfate, which was then filtered and the solvent removed by rotary evaporation to yield (R)-ethyl-3-hydroxybutyrate as a clear oil (20.2 g, 66%).1H NMR (400 MHz, CDCl3): δ=4.1-4.2 (m, 3H), 2.35-2.48 (m,2H), 1.20 (d, J=6.4 Hz, 3H), 1.25 (t, J=6.9 Hz, 3H)13C NMR: (100 MHz, CDCl3): δ=173.04, 64.30, 60.84, 42.89,22.48, 14.24.
With sulfuric acid 2 Synthesis of R-3-hydroxybutyryl R-3-hydroxybutyrate The R-β-butyrolactone underwent smooth reduction with sodium borohydride in ethanol and the resulting R-1,3 butanediol was purified by extraction into 2-propanol from water containing 25% K2HPO4 (12). Esterification of R-β-butyrolactone to R-ethyl 3-hydroxybutyrate with acidic ethanol followed by transesterification with R-1,3 butanediol catalyzed by CAL-B under reduced pressure and solvent-free conditions yields the ketone body ester product R-3-hydroxybutyryl R-3-hydroxybutyrate. The reaction scheme is shown below.
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