Propargyl alcohol → (E)-Tetradec-2-en-1-ol

HRID 1612804Notes

Reaction equation

HRID 1612804 reaction equation
C(O)C#C.[CH2:5]([OH:19])[C:6]#[C:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].COCCO[AlH2-]OCCOC.[Na+]>CCOCC>[CH2:5]([OH:19])/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 109657922-TetradecynolHCID 16684438Red-Al

Product 1

HCID 5353006(E)-Tetradec-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

trans-2-Tetradecen-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 8.0 g (38 mmole) of 2-tetradecyn-1-ol in 30 ml of ether and 16 ml (55 mmole) of Red-Al in 40 ml of ether. Kugelrohr distillation afforded 7.67 g of clear oil. 1H NMR δ5.66 (m, 2), 4.08 (d, 2, J=5 Hz) 2.03 (dd, 2, J=6, 13 Hz), 1.60 (br, 1), 1.4-1.2 (m, 18), 0.88 (t, 3, J=7 HZ).

Workup

  1. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-009fdb88c80546ecabf6c6381fc6036a
Source dataset
uspto-grants-1993_03
Patent number
US05190969

Reaction notes

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