Diethyl Ether → HCID 54493682, compound

HRID 2417750Notes

Reaction equation

HRID 2417750 reaction equation
[OH:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10])([CH:4]=[CH2:5])[CH3:3].C([Li])C[CH2:19][CH3:20].C([C:24]([CH:31]([CH2:33][CH3:34])[CH3:32])([C:28](Cl)=[O:29])[C:25](Cl)=[O:26])C.CC[O:37]CC>>[CH3:32][CH:31]([CH:24]([C:25]([O:1][C:2]([CH3:3])([CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH:4]=[CH2:5])=[O:26])[C:28]([O:29][CH2:19][CH3:20])=[O:37])[CH2:33][CH3:34]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 88883,7,11-Trimethyldodeca-1,6,10-trien-3-olHCID 54509253HCID 54509253, compoundHCID 178418339Butyllithium

Product 1

HCID 54493682HCID 54493682, compound

Procedure

To a solution of nerolidol (5.3 g, 0.024 mole) in 20 ml of dry ether, n-butyllithium (9.6 ml, 0.024 mole, 2.5M in hexane) was added with stirring under a blanket of dry nitrogen. The reaction mixture was cooled by means of a dry ice-acetone bath. Upon completion of addition, ethyl 2-(2-butyl)malonyl chloride (5.0 g, 0.024 mole) was added slowly. After addition was completed, the mixture was allowed to warm to room temperature with stirring for a period of 4 hours.

Workup

  1. temperatureThe reaction mixture was cooled by means of a dry ice-acetone bath
  2. additionwas added slowly
  3. additionAfter addition
  4. stirringwith stirring for a period of 4 hours

Sources & evidence

ORD record
ord-015e592c31af4b909197ca75f4ac8916
Source dataset
uspto-grants-1984_09
Patent number
US04470421

Reaction notes

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