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[ CAS No. 74530-56-6 ] {[proInfo.proName]}

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Product Details of [ 74530-56-6 ]

CAS No. :74530-56-6 MDL No. :MFCD00052188
Formula : C8H13ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DVOUIKQENBFPRS-UHFFFAOYSA-N
M.W : 192.64 Pubchem ID :2724514
Synonyms :

Safety of [ 74530-56-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3265
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 74530-56-6 ]

* 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 [ 74530-56-6 ]

[ 74530-56-6 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 74530-56-6 ]
  • [ 100-51-6 ]
  • [ 95967-46-7 ]
  • 2
  • [ 674-82-8 ]
  • [ 75-65-0 ]
  • [ 74530-56-6 ]
  • tert-butyl 4-chloro-3-hydroxybutanoate [ No CAS ]
  • 3
  • [ 74530-56-6 ]
  • (+/-)-tert-butyl 3,4-epoxybutanoate [ No CAS ]
  • tert-butyl 4-chloro-3-hydroxybutanoate [ No CAS ]
  • 4
  • [ 74530-56-6 ]
  • tert-butyl (R)-(+)-4-chloro-3-hydroxybutanoate [ No CAS ]
  • 5
  • [ 74530-56-6 ]
  • tert-butyl (S)-(-)-4-chloro-3-propanoyloxybutanoate [ No CAS ]
  • 6
  • [ 74530-56-6 ]
  • [ 87064-89-9 ]
  • 7
  • [ 74530-56-6 ]
  • [ 95967-47-8 ]
  • 8
  • [ 74530-56-6 ]
  • [ 95967-28-5 ]
  • 13
  • [ 74530-56-6 ]
  • tert-Butyl 4-chloro-3-hydroxybutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen;bis[(1-isopropyl-4-methylbenzene)dichloro ruthenium]; (+)-Fluoxphos; In ethanol; at 80℃; under 3000.3 Torr; for 4.0h; In a 150 mL autoclave under argon atmosphere [Ru2Cl4(cym)2] (7.7 mg, 0.013 mmol), (+)-Fluoxphos (17.9 mg, 0.026 mmol) and tert-butyl 4-chloro-3-oxobutyrate (assay 96.9% by GC, 1.0 g, 5.2 mmol) is dissolved in degassed ethanol (30 mL). After flushing the autoclave with argon hydrogenation is carried out during 4 hours at 80 C and at 4 bar hydrogen pressure. After cooling to room temperature the reaction solution is directly analyzed by GC for conversion (column: HP-101 25 m / 0.2 mm). Analysis for enantiomeric excess is performed by 1H-NMR using europium(III) tris[3-(trifluoromethyl-hydroxymethylene)-(+)-camphorate] as shift reagent and CDCl3 as solvent. Conversion is >99%. Yield is approx. 67% at an ee of one enantiomer of 93.2%.
  • 14
  • [ 110-89-4 ]
  • [ 74530-56-6 ]
  • [ 75-07-0 ]
  • tert.-butyl 4-chloro-2-ethylidene-3-oxobutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 9 Tert.-butyl 4-chloro-2-ethylidene-3-oxobutyrate STR32 1.5 ml of piperidine are added dropwise to a stirred mixture of 212 g (1.1 mol) of tert.-butyl 4-chloro-3-oxobutyrate and 97 g (2.2 mol) of acetaldehyde at -20 C. under nitrogen.
  • 15
  • silica gel (toluene) [ No CAS ]
  • [ 74530-56-6 ]
  • [ 100-53-8 ]
  • tert-Butyl 4-benzylthioacetoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; water; EXAMPLE 27 STR60 tert.-Butyl 4-benzylthioacetoacetate 7.04 ml (60 mmols) of benzylmercaptan were slowly added dropwise to a suspension of 1.8 g (60 mmols) of sodium hydride (80% in parafin oil) in 50 ml of anhydrous tetrahydrofuran at room temperature. Thereafter, the mixture was subsequently stirred for 15 minutes and then cooled to 0 C. A solution of 10.57 g (55 mmols) of tert.-butyl 4-chloroacetoacetate in 20 ml of tetrahydrofuran was added at this temperature in the course of 1 hour. The ice-bath was removed and the mixture was stirred at room temperature for a further hour and neutralized by addition of a few drops of 10% strength HCl. The solvent was evaporated off in vacuo, ether and water were added to the residue, the mixture was extracted several times with ether and the extracts were washed with water and dried over MgSO4. Evaporation of the ether in vacuo gave an oil, which was purified by chromatography on 800 g of silica gel (toluene). 12.74 g (83%) of the title compound were obtained in the form of a colorless oil. RF: 0.13 (toluene). IR (CHCl3) 1740-1710 cm-1 (C=0, β-ketoester). 1 H-NMR (250 MHz, CDCl3) δ 1.49 (s, 9H, C(CH3)3), 3.22 (s. 2H, CH2), 3.52 (s. 2H, CH2), 3.68 (s. 2H, CH2) and 7.33 (s. 5H, Ph).
In tetrahydrofuran; paraffin; PREPARATION EXAMPLE 7 STR59 tert.-Butyl 4-benzylthioacetoacetate 7.04 ml (60 mmol) of benzylmercaptan were slowly added dropwise to a suspension of 1.8 g (60 mmol) of sodium hydride (80% in liquid paraffin) in 50 ml of anhydrous THF at room temperature. The mixture was then stirred for 15 min and subsequently cooled to 0 C. At this temperature, a solution of 10.57 g (55 mmol) of tert.-butyl 4-chloroacetoacetate in 23 ml of THF was added within 1 h. The icebath was removed, and the mixture was stirred for a further 1 h at room temperature and then neutralized by addition of a few drops of 10% strength HCl. The solvent was evaporated in vacuo, ether was added several times, and the extracts were washed with water and dried over MgSO4. Evaporation of the ether in vacuo produced an oil which was purified by chromatography on 800 g of silica gel (toluene). 12.74 g (83%) of the title compound were obtained in the form of a colorless oil, Rf: 0.13 (toluene). IR (CHCl3) 1740-1710 cm-1 (C=O, β-keto ester). 1 H-NMR (200 MHz, CDCl3) δ 1.49 (s, 9H, C(CH3)3), 3.22 (s, 2H, CH2), 3.52 (s, 2H, CH2), 3.68 (s, 2H, CH2), 7.33 (s, 5H, Ph).
  • 16
  • [ 74530-56-6 ]
  • [ 10387-40-3 ]
  • tert.-butyl 4-acetylthioacetoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; acetonitrile; sodium chloride; EXAMPLE 28 STR61 tert.-Butyl 4-acetylthioacetoacetate 2.40 g (21.0 mmols) of dry potassium thioacetate were added to a solution, cooled to 0 C., of 3.85 g (20.0 mmols) of tert.-butyl 4-chloroacetoacetate in 40 ml of anhydrous acetonitrile and the mixture was stirred at this temperature for 30 minutes. Thereafter, the mixture was poured into a mixture of NaCl solution and ethyl acetate, the organic phase was separated off and extracted with 2*30 ml of ethyl acetate and the extracts were washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been chromatographed on 60 g of silica gel (toluene:ethyl acetate 95:5), 3.87 g (83%) of the title compound were obtained as a colorless oil, RF:0.2 (toluene:ethyl acetate 95:5). IR (CHCl3) 1740-1710 cm-1 (C=0). 1 H-NMR (250 MHz, CDCl3) 1.50 (s. 9H, C(CH3)3), 2.42 (s. 3H, CH3 CO3), 3.53 (s. 2H, CH2) and 3.90 (s, 2H, CH2).
In ethyl acetate; acetonitrile; sodium chloride; PREPARATION EXAMPLE 6 STR58 tert.-Butyl 4-acetylthioacetoacetate 2.40 g (21.0 mmol) of dry potassium thioacetate were added to a solution, which had been cooled to 0 C., of 3.85 g (20.0 mmol) of tert.-butyl 4-chloroacetoacetate in 40 ml of anhydrous acetonitrile, and the mixture was stirred at this temperature for 30 min. It was then poured into a mixture of NaCl solution and ethyl acetate, the organic phase was separated off, extraction with 2*30 ml of ethyl acetate was carried out, and the extract was washed with water and dried over MgSO4. After evaporation of the solvent in vacuo and chromatography of the residue on 60 g of silica gel (toluene:ethyl acetate 95:5), 3.87 g (83%) of the title compound were obtained as a colorless oil, Rf: 0.24 (toluene:ethyl acetate 95:5). IR (CHCl3) 1740-1710 cm-1 (C=O). 1 H-NMR (250 MHz, CDCl3) δ 1.50 (s, 9H, C(CH3)3), 2.42 (s, 3H, CH3 CO), 3.53 (s, 2H, CH2), 3.90 (s, 2H, CH2).
  • 17
  • [ 74530-56-6 ]
  • [ 95967-46-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; benzyl alcohol; In tetrahydrofuran; EXAMPLE 1 STR34 tert.-Butyl 4-benzyloxyacetoacetate A solution of 64.9 g=62.1 ml (0.6 mol) of benzyl alcohol in 50 ml of tetrahydrofuran was added dropwise to an ice-cooled suspension of 18.0 g (0.6 mol) of sodium hydride (80% strength in parafin oil) in 150 ml of anhydrous tetrahydrofuran in the course of 1 hour with ice-cooling. Thereafter, the mixture was subsequently stirred at room temperature for 0.5 hour. A solution of 57.8 g (0.3 mol) of tert.-butyl 4-chloroacetoacetate in 50 ml of tetra-hydrofuran was added dropwise at 0 C. in the course of 1 hour. The ice-bath was removed and the reaction mixture was stirred at room temperature for a further hour and neutralized by careful addition of 0.5N HCl, with cooling (pH control). The mixture was extracted several times with ether and the combined ether extracts were washed with water and dried over MgSO4. Evaporation of the ether in vacuo gave an oil, which was purified by chromatography on 1.7 kg of silica gel (toluene:ethyl acetate 95:5). 41.7 g (53%) of tert.-butyl 4-benzyloxyacetoacetate were obtained, RF: 0.47 (toluene:ethyl acetate 9:1). 1 H-NMR (200 MHz, CDCl3) δ 1.50 (s, 9H, C(CH3)3), 3.48 (s, 2H, CH2), 4.18 (s, 2H, CH2), 4.63 (s, 2H, CH2) and 7.40 (s, 5H, Ph). IR (CHCl3) 1740-1710 (c=0, β-keto ester) and 1656 cm-1 (C=C, enol form). C15 H20 O4 (264.3) calculated: C 68.2, H 7.6; found: C 68.2, H 7.6.
  • 18
  • silica gel (toluene) [ No CAS ]
  • [ 74530-56-6 ]
  • [ 105940-01-0 ]
YieldReaction ConditionsOperation in experiment
PREPARATION EXAMPLE 8 STR60 tert.-Butyl 4-chloro-2-diazo-3-oxobutanoate As described for Preparation Example 1, 2.67 g (84%) of the title compound were obtained as crystals, Rf: 0.29 (toluene), melting point: 40-41 C., from 2.79 g (14.5 mmol) of tert.-butyl 4-chloroacetoacetate and filtration of the crude product on 30 g of silica gel (toluene). IR (CHCl3): 2140 (N2), 1708 (C=O), 1662 cm-1. 1 H-NMR (300 MHz, CDCl3) δ 1.54 (s, 9H, C(CH3)3), 4.60 (s, 2H, CH2).
  • 19
  • [ 74530-56-6 ]
  • [ 2353-44-8 ]
  • 3-(2,4-dioxopyrrolidin-1-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 35 - 125℃; for 7.0h;Inert atmosphere; Reflux; Under a nitrogen atmosphere, 140 g of N,N-dimethylformamide and 12.8 g (0.1 mol) were placed in a 500 ml four-necked flask equipped with a stirring, thermometer and air condenser.3-aminopiperidine-2,6-dione,21.5 g (0.11 mol) of 1-chloroacetoacetic acid tert-butyl ester,40 g of potassium carbonate, stirred at 35 to 40 C for 4 hours,The reaction was stirred at 120 to 125 C for 3 hours.Distilling off the tert-butanol formed by the amidation reaction; cooling to 40 C,21.5 (0.11 mol) of 2-bromo-4-nitro-n-butyraldehyde was added, and the reaction was stirred at 40 to 45 C for 5 hours.Filtered, the filter cake was washed with 40 g of N,N-dimethylformamide.Combine the filtrate,Distillation of N,N-dimethylformamide, addition of 90 g of isopropanol, recrystallization,26.9 g of 3-(7-nitro-3-oxo-1H-isoindol-2-yl)piperidine were obtained -2,6-dione, yield 93.0%, liquid phase purity 99.2%.
  • 20
  • [ 74530-56-6 ]
  • tert-butyl 6-cyano-3,5-dioxo-hexanoate [ No CAS ]
  • 21
  • [ 74530-56-6 ]
  • [ 125971-94-0 ]
  • 22
  • [ 74530-56-6 ]
  • [ 125971-93-9 ]
  • 23
  • [ 74530-56-6 ]
  • [ 125971-86-0 ]
  • 24
  • [ 74530-56-6 ]
  • [ 125971-95-1 ]
  • 25
  • [ 74530-56-6 ]
  • [ 107-21-1 ]
  • [2-chloromethyl-[1,3]-dioxolane-2-yl]acetic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.3% With methanesulfonic acid; at 20 - 60℃; for 6.0h; 50.0 g of t-butyl chloroacetoacetate (1.0 eq),35.5 g of ethylene glycol (2.2 eq) was added to a 500 mL three-necked flask.After the mixture was stirred for 10 minutes, 5.0 g of methanesulfonic acid (0.2 eq) was added.After stirring at room temperature for 3 hours, the mixture was further heated to 50 to 60 C and stirred for 3 hours.The reaction was completed by TLC, and the reaction solution was cooled to room temperature.Add 150 mL of saturated sodium bicarbonate solution, the aqueous phase pH is 7-8. 2×150 mL of ethyl acetate is extracted, and the obtained ethyl acetate layer is combined.Concentration under reduced pressure at 40-50 C gave a pale yellow liquid, 59.8 g, yield 97.3%.
97.3% With methanesulfonic acid; at 20 - 60℃; for 6.0h; 50.0 g of tert-butyl chloroacetoacetate (1.0 eq) and 35.5 g of ethylene glycol (2.2 eq) were added to a 500 mL three-necked flask.After the mixture was stirred for 10 minutes, 5.0 g of methanesulfonic acid (0.2 eq) was added, and the mixture was stirred at room temperature for 3 hours, and then heated to 50 to 60 C for 3 hours.After the TLC monitoring reaction was completed, the reaction solution was cooled to room temperature, and the pH of the aqueous phase was adjusted to 7-8 by adding 150 mL of saturated sodium hydrogencarbonate solution. 2×150 mL of ethyl acetate was extracted, and the obtained ethyl acetate layers were combined and concentrated under reduced pressure at 40-50 C. The pale yellow liquid was 59.8 g, and the yield was 97.3%.
  • 26
  • [ 74530-56-6 ]
  • tert-butyl 6-acetoxy-3,5-dioxohexanoate [ No CAS ]
  • 27
  • [ 74530-56-6 ]
  • (3R,5S)-6-acetoxy-3,5-dihydroxyhexanoic acid tert-butyl ester [ No CAS ]
  • 28
  • [ 74530-56-6 ]
  • [ 154026-95-6 ]
  • 29
  • [ 74530-56-6 ]
  • [ 124752-23-4 ]
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