Quinoline → cis-[3-(3-Hydroxypropenyl)phenoxy]acetic acid tert-butyl ester

HRID 1250112Notes

Reaction equation

HRID 1250112 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[C:11]([O:15][C:16](=[O:29])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26][CH2:27][OH:28])[CH:20]=1)([CH3:14])([CH3:13])[CH3:12].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[C:11]([O:15][C:16](=[O:29])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](/[CH:25]=[CH:26]\[CH2:27][OH:28])[CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 54255612[3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 69992070cis-[3-(3-Hydroxypropenyl)phenoxy]acetic acid tert-butyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

Quinoline (54 μL) and a Lindlar catalyst (54 mg) were added to a stirred solution of [3-(3-hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester (547 mg, 2.09 mmol) in methanol (4.3 mL) under a nitrogen atmosphere. The mixture was stirred for 1 hour in a balloon filled with hydrogen, filtered, and the filtrate was taken to dryness. The residue was purified by flash chromatography, eluting with hexane/ethyl acetate, dissolved in diethyl ether, and washed with 2 N hydrochloric acid (10 mL) and 10% sodium bicarbonate, dried over sodium sulfate, and concentrated to give cis-[3-(3-hydroxypropenyl)phenoxy]acetic acid tert-butyl ester as a colorless oil (420 mg, 76%).

Workup

  1. filtrationfiltered
  2. customThe residue was purified by flash chromatography
  3. washeluting with hexane/ethyl acetate
  4. dissolutiondissolved in diethyl ether
  5. washwashed with 2 N hydrochloric acid (10 mL) and 10% sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f8067f452f284f768a089261f65b7b9a
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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