Tetrahydrofuran → Ethyl acetate ethanol ammonia

HRID 1253746Notes

Reaction equation

HRID 1253746 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1([O:17]C(N(C)C)=[N+](C)C)[C:12]2N=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.C(N(C(C)C)C(C)C)C.[O:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>C(OCC)(=O)C>[C:35]([O:34][CH2:38][CH3:37])(=[O:17])[CH3:36].[CH2:35]([OH:34])[CH3:36].[NH3:8].[CH2:14]1[C:12]2[C:11](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 2

HCID 10326IndaneHCID 86587043Ethyl acetate ethanol ammoniaYield 25%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

General working instructions 4 (GWI-4): O-(7-Azabenzotriazol-1-yl)N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.1 eq.) and N-ethyl-diisopropylamine (2.5 eq.) were added to a solution of the corresponding carboxylic acid (1 eq.) in tetrahydrofuran at 0° C. and the reaction mixture was stirred at room temperature for 0.5 h. The corresponding amine (1 eq.) was then added and the mixture was stirred at room temperature overnight. For working up, the reaction mixture was diluted with ethyl acetate and washed with sat. NaHCO3 solution, NH4Cl solution, dist. water and sat. NaCl solution. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (silica; ethyl acetate/ethanol/ammonia (25% aq.) in order to obtain the product (H) in a pure form.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washwashed with sat. NaHCO3 solution, NH4Cl solution, dist
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica

Sources & evidence

ORD record
ord-d52567fcfab44e5aba4f3f79a3163f19
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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