Tributylphosphine → Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4,7-dimethyl-1-benzofuran-3-yl)acetate

HRID 591469Notes

Reaction equation

HRID 591469 reaction equation
C(P(CCCC)CCCC)CCC.[CH3:14][C:15]1[C:20]([CH2:21][OH:22])=[CH:19][CH:18]=[C:17]([CH3:23])[N:16]=1.[CH3:24][O:25][C:26](=[O:40])[CH2:27][C:28]1[C:32]2[C:33]([CH3:39])=[CH:34][C:35](O)=[C:36]([CH3:37])[C:31]=2[O:30][CH:29]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:24][O:25][C:26](=[O:40])[CH2:27][C:28]1[C:32]2[C:33]([CH3:39])=[CH:34][C:35]([O:22][CH2:21][C:20]3[C:15]([CH3:14])=[N:16][C:17]([CH3:23])=[CH:18][CH:19]=3)=[C:36]([CH3:37])[C:31]=2[O:30][CH:29]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2784752(2,6-Dimethylpyridin-3-yl)methanolHCID 121004234Methyl(6-hydroxy-4,7-dimethyl-1-benzofuran-3-yl)acetate

Product 1

HCID 118667012Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4,7-dimethyl-1-benzofuran-3-yl)acetateYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tri-n-butylphosphine (0.240 mL), (2,6-dimethylpyridin-3-yl)methanol (92 mg), methyl(6-hydroxy-4,7-dimethyl-1-benzofuran-3-yl)acetate (150 mg) and THF (6.0 mL) was added ADDP (242 mg) at room temperature. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The mixture was concentrated. To the residue was added. IPE and the precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (163.9 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. additionTo the residue was added
  3. filtrationIPE and the precipitate was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-a931d0a88c4d43eea053901e77dd409a
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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