Tributylphosphine → Ethyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591392Notes

Reaction equation

HRID 591392 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.[CH2:24]([O:26][C:27](=[O:39])[CH2:28][C:29]1[C:33]2[CH:34]=[CH:35][C:36](O)=[CH:37][C:32]=2[S:31][CH:30]=1)[CH3:25].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH2:24]([O:26][C:27](=[O:39])[CH2:28][C:29]1[C:33]2[CH:34]=[CH:35][C:36]([O:22][CH2:21][C:20]3[C:15]([CH3:14])=[N:16][C:17]([CH3:23])=[CH:18][CH:19]=3)=[CH:37][C:32]=2[S:31][CH:30]=1)[CH3:25]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2784752(2,6-Dimethylpyridin-3-yl)methanolHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

Product 1

HCID 118667000Ethyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetateYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tri-n-butylphosphine (7.10 mL), (2,6-dimethylpyridin-3-yl)methanol (3.00 g), ethyl(6-hydroxy-1-benzothiophen-3-yl)acetate (5.43 g) and THF (150 mL) was added ADDP (7.17 g) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere overnight. The mixture was concentrated. To the residue was added IPE and the precipitate was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (7.74 g)

Workup

  1. concentrationThe mixture was concentrated
  2. additionTo the residue was added IPE
  3. filtrationthe 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-0d5bd81882964de1a6d203eed93a254b
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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