HCID 86635919、化合物 → 3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzaldehyde

HRID 561821ノート

反応式

HRID 561821 の反応式
[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]

参加物

4

反応物 1

HCID 86635919HCID 86635919、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-607f2bc73852406f8be6d204466d4308
出典データセット
uspto-grants-2011_11
特許番号
US08063105B2

反応ノート

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