N,N,N',N'-Tetramethylazodicarboxamide → 2-Methyl-2-{2-methyl-4-[5-(3-trifluoromethoxy-phenyl)-pent-4-ynyloxy]-phenoxy}-propionic acid ethyl ester

HRID 852385Notes

Reaction equation

HRID 852385 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].[F:18][C:19]([F:34])([F:33])[O:20][C:21]1[CH:22]=[C:23]([C:27]#[C:28][CH2:29][CH2:30][CH2:31]O)[CH:24]=[CH:25][CH:26]=1.C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:6])([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:31][CH2:30][CH2:29][C:28]#[C:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([O:20][C:19]([F:18])([F:33])[F:34])[CH:22]=2)=[CH:11][C:10]=1[CH3:16])[CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 688216934-Pentyn-1-ol, 5-[3-(trifluoromethoxy)phenyl]-

Product 1

HCID 694586312-Methyl-2-{2-methyl-4-[5-(3-trifluoromethoxy-phenyl)-pent-4-ynyloxy]-phenoxy}-propionic acid ethyl esterYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of 50 mg (0.21 mmol) 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590), 48 mg (0.21 mmol) 5-(3-trifluoromethoxy-phenyl)-pent-4-yn-1-ol (example 3C]) and 70 μl (0.25 mmol) tributylphosphine (50 19 μmol) in 5 ml tetrahydrofuran were added 43 mg (0.25 mmol) N,N,N′,N′-tetramethyl azodicarboxamide. The cooling bath was removed and stirring continued for 14 h. The mixture was filtered over celite and the solvent removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to obtain 34 mg (80 μmol, 36%) of the title compound as colorless oil.

Workup

  1. customThe cooling bath was removed
  2. filtrationThe mixture was filtered over celite
  3. customthe solvent removed under reduced pressure
  4. customto give a yellow oil which
  5. customwas purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-7143f18e4f75412fb393ee6aa55b687c
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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