2-Methyl-2-pentenal → HCID 68867348, compound

HRID 1725327Notes

Reaction equation

HRID 1725327 reaction equation
[CH3:1][C:2](=[CH:5][CH2:6][CH3:7])[CH:3]=[O:4].[CH:8]1([Mg]Cl)[CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH3:1][C:2]([CH:3]([CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[OH:4])=[CH:5][CH2:6][CH3:7]

Participants

3

Reactant 2

HCID 121772-Methyl-2-pentenalHCID 178478989HCID 178478989, compound

Product 1

HCID 68867348HCID 68867348, compound

Procedure

To a dry 2 liter multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an addition funnel 800 ml of 2 M of cyclopentyl magnesium chloride was added and stirred. 139 g of 2-methyl-2-pentenal was added over the next 90 minutes. The reaction mixture was aged for another 90 minutes and the first sample was taken. 25 minutes later the reaction mixture was quenched with water, aged for 30 minutes and the organic layer was separated and washed with 2 one liter portions of water. The NMR spectrum of the Alpha-[1-Methyl-1-Butenyl]-Cyclopentanemetanol is as follows: 1.00 ppm (s, 3H); 1.1-1.2 ppm (s, 1H); 1.4-1.5 ppm (s, 2H); 1.5-1.7 ppm (m, 4H); 1.8 ppm (s, 1H); 2.1 ppm (m, 3H); 3.7 ppm (d, 1H); 5.4 ppm (t, 1H)

Workup

  1. additionwas added
  2. custom25 minutes later the reaction mixture was quenched with water
  3. waitaged for 30 minutes
  4. customthe organic layer was separated
  5. washwashed with 2 one liter portions of water

Sources & evidence

ORD record
ord-f7ab512ce0e44e0ab9c6154fc5cb8e43
Source dataset
uspto-grants-2009_02
Patent number
US07491684B2

Reaction notes

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