HCID 86635919, compound → 3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzaldehyde

HRID 561821Notes

Reaction equation

HRID 561821 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15](/[CH:17]=[CH:18]/[CH2:19][O:20][CH3:21])[CH:16]=1)[CH:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:16]=1)[CH:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86635919HCID 86635919, compound

Product 1

HCID 866359203-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzaldehyde from Amine 36, Step 3 (1 eq.) in EtOAc (0.1 M) was added palladium (10% w/w over activated carbon, 10% loading). The vessel was evacuated and back filled with hydrogen. The reaction suspension was then stirred under a balloon atmosphere of hydrogen for 1 h. The reaction was quenched with dichloromethane and filtered through a bed of celite. The insolubles were washed further with EtOAc and methanol. Concentration of the filtrate in vacuo and purification of the crude product thus obtained by way of column chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. customThe vessel was evacuated
  2. additionback filled with hydrogen
  3. customThe reaction was quenched with dichloromethane
  4. filtrationfiltered through a bed of celite
  5. washThe insolubles were washed further with EtOAc and methanol
  6. customConcentration of the filtrate in vacuo and purification of the crude product
  7. customthus obtained by way of column chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-607f2bc73852406f8be6d204466d4308
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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