Water → 1309581-54-1

HRID 1525624Notes

Reaction equation

HRID 1525624 reaction equation
Br[C:2]1([O:10][CH2:11][CH2:12][OH:13])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.C1CCN2C(=NCCC2)CC1.CCOC(C)=O.O>CS(C)=O>[CH:2]1([O:10][CH2:11][CH2:12][OH:13])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]#[C:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 68276158HCID 68276158, compound

Product 1

HCID 867123901309581-54-1Yield 74.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Compound 9 (3.76 g, 15.1 mmol) was dissolved in DMSO M, 30 Ml) and heated to 60° C. DBU (4.51 ml, 30.2 mmol, 2.0 eq) was added, the resulting solution was stirred for 15 min and more DBU (18.0 ml, 121 mmol, 8.0 eq) was added. The mixture was stirred at 60° C. overnight and then cooled to RT. EtOAc (100 ml) and water (100 ml) were added. After acidification to pH 1 with concentrated HCl, the aqueous phase was extracted with EtOAc (3×50 ml). The combined organic layers were washed with 1 M HCl/saturated NaCl solution (100 ml each), dried over Na2SO4 and evaporated under reduced pressure. FC (cHex/EtOAc 9:1) afforded compound 10 (1.89 g, 11.2 mmol, 74%) as a light yellow oil.

Workup

  1. stirringThe mixture was stirred at 60° C. overnight
  2. temperaturecooled to RT
  3. extractionAfter acidification to pH 1 with concentrated HCl, the aqueous phase was extracted with EtOAc (3×50 ml)
  4. washThe combined organic layers were washed with 1 M HCl/saturated NaCl solution (100 ml each)
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-17b03917f4494ba5813c0cf2fbdcd8f4
Source dataset
uspto-grants-2015_07
Patent number
US09085514B2

Reaction notes

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