2-Methyl-2-pentenal → HCID 68840668, compound

HRID 1725329Notes

Reaction equation

HRID 1725329 reaction equation
[CH3:1][C:2](=[CH:5][CH2:6][CH3:7])[CH:3]=[O:4].[CH:8]1([Mg]Cl)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([CH:3]([OH:4])[C:2]([CH3:1])=[CH:5][CH2:6][CH3:7])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 121772-Methyl-2-pentenalHCID 178478990HCID 178478990, compound

Product 1

HCID 68840668HCID 68840668, compound

Conditions

Temperature
10 °C

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 cyclohexyl magnesium chloride was added and stirred. The flask was cooled to 10° C. 146 g of 99% 2-methyl-2-pentenal was added over the next 135 minutes. The cooling was removed. The first sample was taken 50 minutes later at 13° C. The second sample was taken 35 minutes later at 18° C. 75 minutes later the reaction mixture was quenched with 1000 ml of 20% HAc with cooling. The layers were allowed to settle and the organic layer extracted with 100 ml of toluene. The NMR spectrum of the 1-cyclohexyl-2-methyl-2-penten-1-ol is as follows . . . 0.7-0.9 ppm (q, 1H); 0.9-1.0 ppm (t, 4H); 1.1-1.3 ppm (m, 3H); 1.6 ppm (s, 3H); 1.6-1.8 ppm (m, 4H); 2.0-2.1 ppm (m, 3H); 3.7 ppm (d, 1H); 5.4 ppm (t, 1H)

Workup

  1. additionwas added
  2. customThe cooling was removed
  3. waitThe second sample was taken 35 minutes later at 18° C
  4. custom75 minutes later the reaction mixture was quenched with 1000 ml of 20% HAc
  5. temperaturewith cooling
  6. extractionthe organic layer extracted with 100 ml of toluene

Sources & evidence

ORD record
ord-5fe0c3cc1649421dbe8958cd7e48f6e1
Source dataset
uspto-grants-2009_02
Patent number
US07491684B2

Reaction notes

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