Triphenylphosphine → HCID 66643841, compound

HRID 1695424Notes

Reaction equation

HRID 1695424 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([OH:10])[CH:9]=1)=[O:4].[CH3:12][C:13]1[O:17][N:16]=[C:15]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:14]=1[CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([O:10][CH2:24][C:14]2[C:15]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:16][O:17][C:13]=2[CH3:12])[CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66643720HCID 66643720, compoundHCID 178498598HCID 178498598, compound

Product 1

HCID 66643841HCID 66643841, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-hydroxy-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (4.68 g, 30 mmol) and [5-methyl-3-(tetrahydro-pyran-4-yl)-isoxazol-4-yl]-methanol (5.92 g, 30 mmol) in THF (400 mL) at 5° C. under argon was added triphenylphosphine (10.6 g, 39 mmol), then diisopropyl azodicarboxylate (8.23 mL, 39 mmol) was added dropwise. The reaction mixture was warmed to room temperature overnight. The reaction mixture was then extracted with ethyl acetate and the organic extract washed with water, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:1) afforded the title compound (7.26 g, 85%) as a white solid. MS: m/e=336.2 [M+H]+.

Workup

  1. extractionThe reaction mixture was then extracted with ethyl acetate
  2. extractionthe organic extract
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-631f1d6c01834e57a56180eeee46147e
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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