Isoprene → 11,11-Diphenylundec-1-ene

HRID 275474ノート

反応式

HRID 275474 の反応式
[Li].[C:2]1([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(OC)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=CC(=C)C.[Cl-].[NH4+]>N.C1COCC1.CO>[C:2]1([CH:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 6557IsopreneHCID 25517Ammonium ChlorideHCID 3028194Lithium2 回HCID 2008832511,11-Diphenyl-11-methoxyundec-1-ene

生成物 1

HCID 2008832411,11-Diphenylundec-1-ene収率 105.4%

試薬・触媒・溶媒 3

HCID 222Ammonia溶媒2 回HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium wire, 0.75 g, was dissolved in 300 mL of ammonia at -78° C. A solution of 10.1 g of 11,11-diphenyl-11-methoxyundec-1-ene in 20 mL of THF to the lithium solution and the mixture was stirred at reflux for 30 min. To a reaction vessel were added sequentially 5 mL isoprene, 5 mL of methanol, and 10 g of ammonium chloride and the ammonia allowed to evaporate at room temperature. Diethyl ether was added to the mixture and the solution was washed with water and brine (saturated aqueous sodium chloride). The organic layer was dried and concentrated in vacuo to give 9.7 g of 11,11-diphenylundec-1-ene which is characterized by:

後処理

  1. temperatureat reflux for 30 min
  2. customto evaporate at room temperature
  3. additionDiethyl ether was added to the mixture
  4. washthe solution was washed with water and brine (saturated aqueous sodium chloride)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-edaa3400d8c9474d95f6de1932f113d0
出典データセット
uspto-grants-1995_02
特許番号
US05393797

反応ノート

読み込み中…