Quinoline → cis-2-Tetradecen-1-ol

HRID 1612800

Reaction equation

HRID 1612800 reaction equation
C(O)/C=C\CCCCCCC.[CH2:12]([OH:26])[C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].N1C2C(=CC=CC=2)C=CC=1>>[CH2:12]([OH:26])/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 7047QuinolineHCID 53649532-Decen-1-ol, (Z)-HCID 109657922-Tetradecynol

Product 1

HCID 13313924cis-2-Tetradecen-1-ol

Procedure

cis-2-Tetradecen-1-ol was prepared as described above for cis-2-decen-1-ol except that 1.0 g of 2-tetradecyn-1-ol, 50 mg of catalyst, and 0.10 ml of quinoline was used. A clear oil, 0.72 g, was obtained after kugelrohr distillation. 1H NMR δ5.57 (m, 2) 4.19 9d, 2, J=6 Hz), 2.07 (dd, 2, J=6, 13 Hz), 1.5-1.2 (m, 18), 0.88 (t, 3, J=7 Hz).

Workup

  1. customA clear oil, 0.72 g, was obtained
  2. distillationafter kugelrohr distillation

Sources & evidence

ORD record
ord-dffb8dfe60534d809cec0bef39e9f88e
Source dataset
uspto-grants-1993_03
Patent number
US05190969

Linked notes

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