Triphenylphosphine → 4-(3,3-Dimethylbut-1-yn-1-yl)benzaldehyde

HRID 128807

反応式

HRID 128807 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][C:30]([CH3:34])([CH3:33])[C:31]#[CH:32]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:29][C:30]([CH3:34])([CH3:33])[C:31]#[C:32][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 707414-Bromobenzaldehyde

生成物 1

HCID 193751604-(3,3-Dimethylbut-1-yn-1-yl)benzaldehyde収率 86%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8471Triethylamine溶媒

実験手順

A mixture of 4-bromobenzaldehyde (3.7 g), triphenylphosphine (0.32 g), palladium(II) acetate (135 mg), and 3,3-dimethyl-1-butyne (4 ml) in triethylamine (20 ml) is thoroughly purged with nitrogen, then heated to 100° in a sealed tube under nitrogen for 2 hr. The mixture is cooled, and the precipitated triethylamine hydrobromide is removed by filtration. The filtrate is concentrated, and the residue dissolved in 3:1 dichloromethane-hexane and filtered through a 2-cm pad of silica gel. The filtrate is concentrated and vacuum-distilled to provide 4-(3,3-dimethyl-1-butynyl)benzaldehyde as a pale yellow solid (3.25 g, 86%).

後処理

  1. customis thoroughly purged with nitrogen
  2. temperatureheated to 100° in a sealed tube under nitrogen for 2 hr
  3. temperatureThe mixture is cooled
  4. customthe precipitated triethylamine hydrobromide is removed by filtration
  5. concentrationThe filtrate is concentrated
  6. dissolutionthe residue dissolved in 3:1 dichloromethane-hexane
  7. filtrationfiltered through a 2-cm pad of silica gel
  8. concentrationThe filtrate is concentrated
  9. distillationvacuum-distilled

出典と根拠

ORDレコード
ord-36d789816f734a5da602139274dad03b
出典データセット
uspto-grants-1995_11
特許番号
US05464865

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