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Chemical Structure| 771430-70-7 Chemical Structure| 771430-70-7

Structure of 771430-70-7

Chemical Structure| 771430-70-7

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Product Details of [ 771430-70-7 ]

CAS No. :771430-70-7
Formula : C6H10O2
M.W : 114.14
SMILES Code : OCC(CC#C)CO

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Application In Synthesis of [ 771430-70-7 ]

* 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 [ 771430-70-7 ]

[ 771430-70-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 771430-70-7 ]
  • [ 147751-16-4 ]
  • [ 1039434-01-9 ]
YieldReaction ConditionsOperation in experiment
A solution comprising the diol, 2-prop-2-yn-l-ylpropane-l,3-diol (0.5g; 4.381 mmol) from (Example 24, Step A), triphenylphosphine (2.53g; 9.637 mmol) and <strong>[147751-16-4]tert-butyl (methylsulfonyl)carbamate</strong> (1.8g; 9.199 mmol) in dry CH2CI2 (30 ml) was stirred at O0C in an ice- water bath. Neat di-isopropylazodicarboxylate (2.16 ml; 10.951 mmol) was added drop by drop to the solution over 10 minutes and the reaction mixture stirred for 4h during which time the ice- water bath had melted and had risen to room temperature. The progress of the reaction was checked by lc-ms (m/z = 491.1 M+Na). The reaction solution was then evaporated under reduced pressure on a rotary evaporator. The crude product was purified by preparative tic on silica gel plates eluted with EtOAc: Hex 1 :4 v/v to give an oil. The product by NMR was still contaminated with di-isopropyl hydrazine- 1 ,2-dicarboxylate. The oil was triturated with EtOAc:Hex (5:95 v/v) and crystallization induced by scratching. A copious white precipitate appeared. The solid was filtered off and the filtrates thus obtained (mixture of the desired bis- methanesulfonate and hydrazine- 1 ,2-dicarboxylate (approx. 1 : 1) was concentrated under reduced pressure and the residues taken on to the deprotection step. The oil was dissolved in dry CH2CI2(5 ml) and anisole (1 ml) was added followed by trifluoroacetic acid (5 ml). The reaction mixture was stirred as a solution overnight at room temperature. After 18 hours, the volatiles were removed on a rotary evaporator under reduced pressure to leave an oil. The oil was partitioned with IN aqueous sodium hydroxide solution (50 ml) and ether (2 x 50 ml). The ethereal extracts were combined and dried over anhydrous MgStheta4 powder, filtered and the filtrates concentrated under reduced pressure. The oil residue from evaporation was purified by preparative tic on silica gel plates that were eluted with EtOAc : Hexanes (1 :3 v/v) to afford the title compound. 1H-NMR (400 MHz, CDCl3) delta: 2.08 (complex., 2H), 2.30 (dd, J = 2.5Hz and 7Hz 2H), 2.99 (s, 6H), 3.25 (m, 2H), 3.34 (m, 2H), 4.90 (broad t, 2H)
 

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