Diketene → HCID 21932485, compound

HRID 1870703Notes

Reaction equation

HRID 1870703 reaction equation
[CH3:1][CH:2]([CH:10]=[CH2:11])[CH2:3][CH2:4][CH2:5][C:6]([OH:9])([CH3:8])[CH3:7].[CH2:12]=[C:13]1[O:17][C:15](=[O:16])[CH2:14]1>CN(C)C1C=CN=CC=1>[O:17]=[C:13]([CH3:12])[CH2:14][C:15]([O:9][C:6]([CH3:7])([CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH:10]=[CH2:11])[CH3:8])=[O:16]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 290961,1,5-Trimethyl-6-heptenol

Product 1

HCID 21932485HCID 21932485, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
55 °C

Procedure

A mixture of dihydromyrcenol (37.88 g, 0.240 mol) and 4-dimethylaminopyridine (0.16 g, 1.30 mmol) in a 100 mL three-necked round-bottomed flask fitted with a condenser, argon inlet, addition funnel, magnetic stirrer and internal thermometer is heated to 50-60° C. Diketene (20.16 g, 0.240 mol) is added dropwise in the course of 15 min. The mixture has a slight exotherm and turned from yellow to red during this time. After stirring an additional hour at 50° C., the mixture is cooled to room temperature. At this point, NMR analysis indicates the reaction is complete. Purification of the product mixture by flash chromatography (elution with dichloromethane) yields the desired product in 95% yield as a nearly colorless oil.

Workup

  1. customfitted with a condenser, argon inlet, addition funnel, magnetic stirrer
  2. temperaturethe mixture is cooled to room temperature
  3. customPurification of the product mixture
  4. washby flash chromatography (elution with dichloromethane)

Sources & evidence

ORD record
ord-7ac4e1edabfc46c78067f1dc5735bd8c
Source dataset
uspto-grants-2000_08
Patent number
US06100233

Reaction notes

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