Tetrahydrofuran → 3-[3,4-Dichloro-5-(hydroxymethyl)phenyl]propanenitrile

HRID 337589Notes

Reaction equation

HRID 337589 reaction equation
C1COCC1.[Cl:6][C:7]1[CH:8]=[C:9]([CH2:23][CH2:24][C:25]#[N:26])[CH:10]=[C:11]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[C:12]=1[Cl:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOCC>[Cl:6][C:7]1[CH:8]=[C:9]([CH2:23][CH2:24][C:25]#[N:26])[CH:10]=[C:11]([CH2:14][OH:15])[C:12]=1[Cl:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 668961283-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]propanenitrile

Product 1

HCID 668954223-[3,4-Dichloro-5-(hydroxymethyl)phenyl]propanenitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a THF (0.1 M) solution of 3-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]propanenitrile (1 eq.) from the previous step was added TBAF (1.0 M THF solution, 1.2 eq.). The resulting solution was stirred at RT for 3 h. The reaction was then diluted with ether and quenched with water. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customquenched with water
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-51df872078704a2b92156708516e99fa
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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