Methanol → 1,1-Diphenyl-10-undecen-1-ol

HRID 273821ノート

反応式

HRID 273821 の反応式
[C:1]([O:13]CC)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO>C1COCC1>[C:16]1([C:1]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 887MethanolHCID 12729Ethyl 10-undecenoateHCID 178418255HCID 178418255、化合物

生成物 1

HCID 200883261,1-Diphenyl-10-undecen-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 10.6 g of ethyl undecylenate in 100 mL of THF at 0° C. was added, over 1 hr, 40 mL of 3M phenyl magnesium bromide. The mixture was warmed to room temperature and stirred for 75 hrs. Methanol, 10 mL, was added to quench the excess Grinard reagent and the solvent was distilled in vacuo. The residue was shaken with diethyl ether and dilute hydrochloric acid. The ether layer was washed with water and saturated sodium hydrogen carbonate, dried, and concentrated in vacuo to give 18.3 g of crude product, which was then chromatographed on silica gel with chloroform as the eluent, to give 13.7 g of 1,1-diphenyl-10-undecen-1-ol which is characterized by:

後処理

  1. customto quench the excess Grinard reagent
  2. distillationthe solvent was distilled in vacuo
  3. stirringThe residue was shaken with diethyl ether and dilute hydrochloric acid
  4. washThe ether layer was washed with water and saturated sodium hydrogen carbonate
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give 18.3 g of crude product, which
  8. customwas then chromatographed on silica gel with chloroform as the eluent

出典と根拠

ORDレコード
ord-b9fb1a3b9bda4b179a505a0433bf8244
出典データセット
uspto-grants-1995_02
特許番号
US05387617

反応ノート

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