Water → Ethyl 3-(3-((dimethylamino)methyl)-4-hydroxyphenyl)-2-methylpropanoate

HRID 1876404

Reaction equation

HRID 1876404 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[CH3:23][N+:24](=[CH2:26])[CH3:25].O>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH2:26][C:7]1[CH:6]=[C:5]([CH2:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=[CH:3][C:2]=1[OH:1])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2724133Dimethyl(methylene)ammounium iodideHCID 20748401Ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate

Product 1

HCID 58566359Ethyl 3-(3-((dimethylamino)methyl)-4-hydroxyphenyl)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate (672) (150 mg, 0.72 mmol), potassium carbonate (149.3 mg, 1.08 mmol) in toluene (7 mL) was added N,N-dimethylmethylideneammonium iodide (173.2 mg, 0.94 mmol) and stirred for 72 hours. Water was added and the reaction was extracted with ethyl acetate and the combined organic layers dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%) to give ethyl 3-(3-((dimethylamino)methyl)-4-hydroxyphenyl)-2-methylpropanoate (673).

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. dry with materialthe combined organic layers dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%)

Sources & evidence

ORD record
ord-eac68235966345758a0c07d7003749e2
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Linked notes

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