Tributylphosphine → Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-vinyl-1-benzothiophen-3-yl)acetate

HRID 591414Notes

Reaction equation

HRID 591414 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:9]2[C:10]([CH:15]=[CH2:16])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1.[CH3:18][C:19]1[C:24]([CH2:25]O)=[CH:23][CH:22]=[C:21]([CH3:27])[N:20]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C(P(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:9]2[C:10]([CH:15]=[CH2:16])=[CH:11][C:12]([O:14][CH2:25][C:24]3[C:19]([CH3:18])=[N:20][C:21]([CH3:27])=[CH:22][CH:23]=3)=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2784752(2,6-Dimethylpyridin-3-yl)methanolHCID 89767599Methyl(6-hydroxy-4-vinyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 118667004Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-vinyl-1-benzothiophen-3-yl)acetateYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(6-hydroxy-4-vinyl-1-benzothiophen-3-yl)acetate (351 mg) and THF (dry) (3 mL) were added (2,6-dimethylpyridin-3-yl)methanol (233 mg), ADDP (535 mg) and tri-n-butylphosphine (0.523 mL) at room temperature. The precipitate was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (459 mg).

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-85ea7c58359243b08a66f126a9825931
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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