Undec-2-yn-1-ol → 75039-83-7

HRID 2255028Notes

Reaction equation

HRID 2255028 reaction equation
[CH2:1]([OH:12])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>CCOC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([OH:12])/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 1

HCID 182209Undec-2-yn-1-ol

Product 1

HCID 1264242575039-83-7

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-Undecyn-1-ol (48) (0.5 g, 3 mmol) in EtOAc (10 mL) was added Lindlar catalyst (25 mg). Hydrogen was bubbled through the reaction mixture. After 2 hours, the reaction was judged complete by TLC (90:10 EtOAc/Petroleum ether, Rf (13)=0.61, Rf (14)=0.55). The reaction mixture was filtered and the filtrate was concentrated by rotary evaporation to yield cis-2-Undecen-1-ol (14) as a colorless oil: 1H NMR (CDCl3) δ 5.60 (m, 2 H), 4.21 (s, 2 H), 2.14 (m, 2 H), 1.35 (m, 12 H), 0.82 (t, J=6.9 Hz, 3 H); 13C NMR (CDCl3) δ 132.98, 128.32, 58.42, 31.85, 29.57, 29.29, 29.19, 27.38, 22.63, 14.04. ##STR23##

Workup

  1. customHydrogen was bubbled through the reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-2badb04ce515458b9718e765233dea8f
Source dataset
uspto-grants-1993_08
Patent number
US05238832

Reaction notes

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