Tyrosol → HCID 68935235, compound

HRID 916850Notes

Reaction equation

HRID 916850 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:2][CH2:3][O:4][CH2:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[C:9]#[N:10])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 10393TyrosolHCID 11430Potassium CarbonateHCID 68939004HCID 68939004, compound

Product 1

HCID 68935235HCID 68935235, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-[(2-bromoethoxy)methyl]benzonitrile (5.00 g), 2-(4-hydroxyphenyl)ethanol (3.45 g), and potassium carbonate (5.76 g) in N,N-dimethylformamide (30 ml) was heated at 60° C. for 66 h. The mixture was allowed to cool and partitioned between ethyl acetate and 2N HCl. The aqueous phase was extracted with ethyl acetate and the combined organic phase washed with 2N NaOH, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (SPE, eluted with gradient between cyclohexane and 80% EtOAc in cyclohexane) to give the title compound (5.05 g). LCMS RT=2.96 min.

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate and 2N HCl
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phase washed with 2N NaOH, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (SPE, eluted with gradient between cyclohexane and 80% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-94531d4bfc684eeebc56a01e4f75bd7e
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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