Propargyl alcohol → 2-Decenol, (2E)-

HRID 1858889

反応式

HRID 1858889 の反応式
C(O)C#C.[CH2:5]([OH:15])[C:6]#[C:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].COCCO[AlH2-]OCCOC.[Na+]>CCOCC>[CH2:5]([OH:15])/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

5

反応物 3

HCID 7859Propargyl alcoholHCID 777632-Decyn-1-olHCID 16684438Red-Al

生成物 1

HCID 53649422-Decenol, (2E)-

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

trans-2-Decen-1-ol was prepared by reduction of the propargyl alcohol by the method described by Jones and Denmark (Org. Syn., 1985, 64, 182-8) using 15 g (97 mmole) of 2-decyn-1-ol in 40 ml of ether and 48 ml (162 mmole) of Red-Al (sodium bis(2-methoxyethoxy)aluminum hybride) in 50 ml of ether. Kugelrohr distillation afforded 11.59 g of a clear oil. 1H NMR δ 5.66 (m, 2), 4.07 (d, 2, J=5 Hz), 20.3 (dd, 2, J=6, 13 hz), 1.68 (br, 1), 1.4-1.2 (m, 10), 0.88 (t, 3, J=7 Hz).

後処理

  1. distillationKugelrohr distillation

出典と根拠

ORDレコード
ord-5195efbe7d07416d8daebeddd5da6074
出典データセット
uspto-grants-2000_11
特許番号
US06153589

関連ノート

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