Ethyl 3-[2-(2,2-diethylpropyl)benzoxazol-5-yl]propenoate → Ethyl 3-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]propanoate

HRID 48168Notes

Reaction equation

HRID 48168 reaction equation
[CH2:1]([C:3]([CH2:22]C)([CH3:21])[CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][C:8]=2[N:9]=1)C>C(O)C.[Pd]>[CH3:1][C:3]([CH3:21])([CH3:22])[CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][C:8]=2[N:9]=1

Participants

4

Reactant 1

HCID 69894701Ethyl 3-[2-(2,2-diethylpropyl)benzoxazol-5-yl]propenoate

Product 1

HCID 22742095Ethyl 3-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]propanoateYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-[2-(2,2-diethylpropyl)benzoxazol-5-yl]propenoate (0.500 g, 0.00174 mol) in ethanol (30 ml) was hydrogenated at 4.0 bar (4×105 Nm−2) over 5% Pd on C for 4 hours at room temperature and then at 5.5 bar (5.5×105 Nm−2) for 6 hours. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate:dichloromethane 3:97, to give ethyl 3-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]propanoate (0.465 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with ethyl acetate:dichloromethane 3:97

Sources & evidence

ORD record
ord-facc77fea7db4e5ea28bb072879bb77f
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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