Triethylamine → Ethyl 4-(4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutanoate

HRID 1860676Notes

Reaction equation

HRID 1860676 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[C:6]([OH:10])[C:5](Br)=[CH:4][C:3]=1[CH2:12][C:13]([CH3:21])([CH3:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>C(O)C.[Pd]>[OH:10][C:6]1[CH:5]=[CH:4][C:3]([CH2:12][C:13]([CH3:20])([CH3:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:2][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18624190Ethyl 4-(2,5-dibromo-4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutanoate

Product 1

HCID 18624199Ethyl 4-(4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutanoateYield 54.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of STEP 5 (0.525 g, 1.3 mmol), 20% Pd/C, triethylamine (0.39 g, 3.9 mmol) in ethanol was subjected to hydrogenation conditions at 40 psi and room temperature for 1 h. The reaction was filtered through a short column of Celite® and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/3) to afford 0.19 g colorless oil. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. filtrationThe reaction was filtered through a short column of Celite®
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-9b145c4024954c0ba2e80285c51ecb71
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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