Cyclododeca-4,8-diene-1-carbaldehyde → 1-(4,8-Cyclododecadienyl)-2-methyl-1-propanol

HRID 1266957ノート

反応式

HRID 1266957 の反応式
[CH:1]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[CH:15]([Mg]Cl)([CH3:17])[CH3:16]>C1COCC1>[CH:1]1([CH:13]([OH:14])[CH:15]([CH3:17])[CH3:16])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 54140259Cyclododeca-4,8-diene-1-carbaldehydeHCID 178418918HCID 178418918、化合物

生成物 1

HCID 541109191-(4,8-Cyclododecadienyl)-2-methyl-1-propanol収率 65.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4,8-Cyclododecadiene carboxaldehyde (QRM 2185) [14.0 g; 0.072 mol] was dissolved in THF (50 ml), and isopropylmagnesium chloride [36 ml; 2.0 M in Et2O, 0.072 mol] was added dropwise with stirring under N2. The reaction mixture was stirred for 30 minutes, most solvent was removed in vacuo, and the residue quenched with saturated ammonium chloride solution, then partitioned (Et2O/H2O). The organic layer was separated, washed and dried over MgSO4. The solvent was removed in vacuo, and the residue was chromatographed [silica: Et2O 50%, hexane 50%] to give 1-(4,8-cyclododecadienyl)-2-methyl-1-propanol (11.1 g, 65%) as a colourless oil.

後処理

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. custommost solvent was removed in vacuo
  3. customthe residue quenched with saturated ammonium chloride solution
  4. custompartitioned (Et2O/H2O)
  5. customThe organic layer was separated
  6. washwashed
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customthe residue was chromatographed [silica: Et2O 50%, hexane 50%]

出典と根拠

ORDレコード
ord-1a92c369d76f40aab6ce5a48e1ba8d4d
出典データセット
uspto-grants-2003_04
特許番号
US06551988B1

反応ノート

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