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Chemical Structure| 1185387-66-9 Chemical Structure| 1185387-66-9

Structure of 1185387-66-9

Chemical Structure| 1185387-66-9

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Product Details of [ 1185387-66-9 ]

CAS No. :1185387-66-9
Formula : C7H12O3
M.W : 144.17
SMILES Code : O=C(OCC)C(C1CC1)O
MDL No. :MFCD16693995
InChI Key :KTPCONMBPLSHRU-UHFFFAOYSA-N
Pubchem ID :62215201

Safety of [ 1185387-66-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P330-P501

Application In Synthesis of [ 1185387-66-9 ]

* 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 [ 1185387-66-9 ]

[ 1185387-66-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1185387-66-9 ]
  • [ 1200828-74-5 ]
YieldReaction ConditionsOperation in experiment
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 2h; A flame dried two-neck round bottom flask fitted with a reflux condenser and N2 outlet was charged with anhydrous THF, freshly activated Mg (120 mg, 4.95 mmol) and a catalytic amount of iodine. A small portion of cyclopropyl bromide dissolved in THF was added. Afier initiation of reflux, the reaction mixture was cooled to -20 C. and the remaining cyclopropyl bromide (500 mg, 4.13 mmol) was gradually added. Afier 30 mm a freshly distilled solution of glyoxalate 45 (549 mg, 5.37 mmol) in THF was added over a 10 mm period and the resulting solution was stirred at -20 C. for 2 h before being quenched with a small amount of watet After 10 mm the reaction mixture was thrther diluted with water (50 mL) and extracted with ethyl acetate (3x50 mL). The organic extracts were combined, dried over anhydrous Mg504, filtered, concentrated in vacuo and purifiedby column chromatography eluting with ethyl acetate/nhexane (a gradient of 10-20%) to furnish ethyl a-hydroxy132 cyclopropaneacetate (422 mg, 71%) as a viscous oil. The oil (350 mg, 2.43 mmol) was dissolved in anhydrous DCM and cooled to 0 C. Then Ph3P (2.04 gm, 7.78 mmol) was added followed by C13r4 (1.20 gm, 3.64 mmol). The reactionmixture was stirred at 0 C. for 2 h and then concentrated in vacuo. The Ph3PO was precipitated by addition of n-hexane and removed by filtration. The crude reaction mixture was purified by flash column chromatography to furnish ethyl a-bromocyclopropaneacetate (46, R=c-Pr): (311 mg, 62%yield).
 

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