Triphenylphosphine → HCID 45376865, compound

HRID 1260376

Reaction equation

HRID 1260376 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C([O:16][C:17]1[CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24])(=O)C.[CH3:37][C:38]1[O:42][C:41]([CH2:43]O)=[CH:40][CH:39]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)Cl>[OH:16][C:17]1[CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:43][C:41]3[O:42][C:38]([CH3:37])=[CH:39][CH:40]=3)[CH:31]=2)=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5209115-Methylfurfuryl alcoholHCID 5462977Diethyl azodicarboxylateHCID 67340885HCID 67340885, compound

Product 1

HCID 45376865HCID 45376865, compoundYield 1.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (1.13 mL 5.83 mmol) was added dropwise to a solution of (E)-3-(3-acetoxy-4-methoxy-phenyl)-N-(3-hydroxy-phenyl)-acrylamide (0.763 g, 2.33 mmol), (5-methyl-furan-2-yl)-methanol (0.392 g, 3.5 mmol) and triphenylphosphine (1.53 g, 5.83 mmol) in dry THF (20 mL) at 0° C. The resulting solution was allowed to reach RT and stirred for 16 hrs. The reaction mixture was then diluted with DCM and washed with water, aqueous hydrochloric acid, and brine. The organic layer was then dried over sodium sulphate and evaporated. The resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols) and stirred at RT for 16 hrs, concentrated under reduced pressure, taken up with solvent an re-evaporated (3 times with MeOH and once with acetone) to give a residue that was purified by silica gel column chromatography (eluant DCM/MeOH 98/2) to obtain 15 mg of the title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[3-(5-methyl-furan-2-ylmethoxy)-phenyl]-acrylamide.

Workup

  1. customto reach RT
  2. washwashed with water, aqueous hydrochloric acid, and brine
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. customevaporated
  5. customThe resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols)
  6. stirringstirred at RT for 16 hrs
  7. concentrationconcentrated under reduced pressure
  8. customan re-evaporated (3 times with MeOH
  9. customonce with acetone) to give a residue that
  10. customwas purified by silica gel column chromatography (eluant DCM/MeOH 98/2)

Sources & evidence

ORD record
ord-e24d35545ead4be29c57e45cb170b1d1
Source dataset
uspto-grants-2013_06
Patent number
US08470831B2

Linked notes

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