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

HRID 561821노트

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HRID 561821 반응식
[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]

참가 물질

4

반응물 1

HCID 86635919HCID 86635919, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-607f2bc73852406f8be6d204466d4308
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063105B2

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