Triethylamine → 3-(1-Undecynyl)benzaldehyde

HRID 235173

反応式

HRID 235173 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(N(CC)CC)C>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I>[C:10]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 752491-UndecyneHCID 765833-Bromobenzaldehyde

生成物 1

HCID 183730913-(1-Undecynyl)benzaldehyde収率 13.2%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

A mixture of 3-bromobenzaldehyde (51.8 g), 1-undecyne (48.6 g), bis(triphenylphosphine)palladium(II)chloride (3.37 g), copper iodide (457 mg), and triethylamine (196 ml) in dry tetrahydrofuran (300 ml) was stirred for 4 hrs at 55° C. The reaction mixture was filtered, the filtrate was diluted with ethyl acetate, and the solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on 300 g of silica gel (1:4-ethyl acetate:hexane). The appropriate fractions were collected and evaporated. Distillation of a 40-g sample of the residue (81.3 g) gave 9.5 g (13%) of the product, bp 172°-174° C. (0.5 mm mercury).

後処理

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washthe solution was washed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed on 300 g of silica gel (1:4-ethyl acetate:hexane)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. distillationDistillation of a 40-g sample of the residue (81.3 g)

出典と根拠

ORDレコード
ord-bbdebe7d835e47279cfb8806cde1fdf0
出典データセット
uspto-grants-1997_01
特許番号
US05597838

関連ノート

読み込み中…