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[ CAS No. 35249-73-1 ] {[proInfo.proName]}

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Chemical Structure| 35249-73-1
Chemical Structure| 35249-73-1
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Product Details of [ 35249-73-1 ]

CAS No. :35249-73-1 MDL No. :MFCD27949816
Formula : C9H7ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 198.60 Pubchem ID :-
Synonyms :

Safety of [ 35249-73-1 ]

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Precautionary Statements: UN#:
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Application In Synthesis of [ 35249-73-1 ]

* 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 [ 35249-73-1 ]

[ 35249-73-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 24867-26-3 ]
  • [ 35249-73-1 ]
  • N-[4-(Benzyloxyoxalyl-amino)-6-piperidin-1-yl-pyrimidin-2-yl]-oxalamic acid benzyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1057 - 1067
  • 2
  • [ 79-37-8 ]
  • [ 100-51-6 ]
  • [ 7579-36-4 ]
  • [ 35249-73-1 ]
YieldReaction ConditionsOperation in experiment
Oxalyl chloride (1 mL) was cooled to 0 C, and anhydrous benzyl alcohol (1.4 mL) added dropwise over 15 min. After the addition of the alcohol was completed, the reaction mixture was warmed up to room temperature and stirred for 1.5 h. The resulting mixture was analysed by 1H and 13C NMR spectroscopyand found to be a mixture of the oxalic acidmonobenzyl ester monochloride and the dibenzyl oxalate in a 5:1 molar ratio. The mixture was used in the next step immediately without further purification. 1H NMR (300 MHz, 297 K,CDCl3, delta, ppm) 7.47-7.42 (m, 5H), 7.42-7.38 (m, 1.75 H), 5.38(s, 2H), 5.32 (s, 0.72 H); 13C NMR (75 MHz, 297 K, CDCl3, delta,ppm) 160.95, 157.57, 155.53, 134.18, 133.33, 129.35, 128.91,128.78, 128.74, 70.38, 68.63.
Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 332 - 343
  • 3
  • [ 77-53-2 ]
  • [ 35249-73-1 ]
  • benzyl ((3R,3aS,6R,7R,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl)oxalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With pyridine; In diethyl ether; at 23℃; for 1h; General procedure: B1. Benzyl alcohol (1.0 equiv) in dry Et2O (0.3 M) was added dropwise over 1 h to an ice-cooled solution of oxalyl chloride (2.0 equiv) in dry Et2O (0.6 M). The resulting solution was stirred for 1 h after addition. The reaction mixture was then concentrated to give a slightly yellow oil that was dried in vacuo to remove traces of oxalyl chloride. In a separate round-bottom flask, the substrate alcohol (1.0 equiv) and pyridine (1.2 equiv) were dissolved in dry Et2O (0.1 M). A solution of the benzyl chlorooxoacetate in a minimal amount of Et2O was added dropwise at 23C, causing the formation of a white precipitate. The resulting mixture was stirred for 1 h. Upon completion, the reaction mixture was transferred to a separatory funnel and washed successively with water and brine. The organic phase was dried over MgSO4, filtered and concentrated to afford the desired alkyl benzyl oxalate, which was purified by flash column chromatography over silica gel.
Reference： [1]Tetrahedron,2019,vol. 75,p. 4222 - 4227
  • 4
  • [ 556-48-9 ]
  • [ 35249-73-1 ]
  • benzyl (4-hydroxycyclohexyl) oxalate [ No CAS ]
  • dibenzyl O,O'-(cyclohexane-1,4-diyl) dioxalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 35% 2: 25% With pyridine In diethyl ether at 23℃; for 1h; 3.2. General Procedure B. Synthesis of oxalic acids via alkyl benzyl oxalates. General procedure: B1. Benzyl alcohol (1.0 equiv) in dry Et2O (0.3 M) was added dropwise over 1 h to an ice-cooled solution of oxalyl chloride (2.0 equiv) in dry Et2O (0.6 M). The resulting solution was stirred for 1 h after addition. The reaction mixture was then concentrated to give a slightly yellow oil that was dried in vacuo to remove traces of oxalyl chloride. In a separate round-bottom flask, the substrate alcohol (1.0 equiv) and pyridine (1.2 equiv) were dissolved in dry Et2O (0.1 M). A solution of the benzyl chlorooxoacetate in a minimal amount of Et2O was added dropwise at 23°C, causing the formation of a white precipitate. The resulting mixture was stirred for 1 h. Upon completion, the reaction mixture was transferred to a separatory funnel and washed successively with water and brine. The organic phase was dried over MgSO4, filtered and concentrated to afford the desired alkyl benzyl oxalate, which was purified by flash column chromatography over silica gel.
Reference： [1]González-Esguevillas, María; Miró, Javier; Jeffrey, Jenna L.; MacMillan, David W.C. [Tetrahedron, 2019, vol. 75, # 32, p. 4222 - 4227]
  • 5
  • [ 504-01-8 ]
  • [ 35249-73-1 ]
  • benzyl (3-hydroxycyclohexyl) oxalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With pyridine; In diethyl ether; at 23℃; for 1h; General procedure: B1. Benzyl alcohol (1.0 equiv) in dry Et2O (0.3 M) was added dropwise over 1 h to an ice-cooled solution of oxalyl chloride (2.0 equiv) in dry Et2O (0.6 M). The resulting solution was stirred for 1 h after addition. The reaction mixture was then concentrated to give a slightly yellow oil that was dried in vacuo to remove traces of oxalyl chloride. In a separate round-bottom flask, the substrate alcohol (1.0 equiv) and pyridine (1.2 equiv) were dissolved in dry Et2O (0.1 M). A solution of the benzyl chlorooxoacetate in a minimal amount of Et2O was added dropwise at 23C, causing the formation of a white precipitate. The resulting mixture was stirred for 1 h. Upon completion, the reaction mixture was transferred to a separatory funnel and washed successively with water and brine. The organic phase was dried over MgSO4, filtered and concentrated to afford the desired alkyl benzyl oxalate, which was purified by flash column chromatography over silica gel.
Reference： [1]Tetrahedron,2019,vol. 75,p. 4222 - 4227
  • 6
  • [ 18267-36-2 ]
  • [ 35249-73-1 ]
  • benzyl (4-ethoxy-2-methyl-4-oxobutan-2-yl) oxalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With pyridine In diethyl ether at 23℃; for 1h; 3.2. General Procedure B. Synthesis of oxalic acids via alkyl benzyl oxalates. General procedure: B1. Benzyl alcohol (1.0 equiv) in dry Et2O (0.3 M) was added dropwise over 1 h to an ice-cooled solution of oxalyl chloride (2.0 equiv) in dry Et2O (0.6 M). The resulting solution was stirred for 1 h after addition. The reaction mixture was then concentrated to give a slightly yellow oil that was dried in vacuo to remove traces of oxalyl chloride. In a separate round-bottom flask, the substrate alcohol (1.0 equiv) and pyridine (1.2 equiv) were dissolved in dry Et2O (0.1 M). A solution of the benzyl chlorooxoacetate in a minimal amount of Et2O was added dropwise at 23°C, causing the formation of a white precipitate. The resulting mixture was stirred for 1 h. Upon completion, the reaction mixture was transferred to a separatory funnel and washed successively with water and brine. The organic phase was dried over MgSO4, filtered and concentrated to afford the desired alkyl benzyl oxalate, which was purified by flash column chromatography over silica gel.
Reference： [1]González-Esguevillas, María; Miró, Javier; Jeffrey, Jenna L.; MacMillan, David W.C. [Tetrahedron, 2019, vol. 75, # 32, p. 4222 - 4227]

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