Diethyl Ether → HCID 53853733, compound

HRID 2417749Notes

Reaction equation

HRID 2417749 reaction equation
[CH3:1][C:2]([OH:6])([CH:4]=[CH2:5])[CH3:3].C([Li])C[CH2:9][CH3:10].C([C:14]([CH:21]([CH2:23][CH3:24])[CH3:22])([C:18](Cl)=[O:19])[C:15](Cl)=[O:16])C.CC[O:27]CC>>[CH3:22][CH:21]([CH:14]([C:15]([O:6][C:2]([CH3:3])([CH:4]=[CH2:5])[CH3:1])=[O:16])[C:18]([O:19][CH2:9][CH3:10])=[O:27])[CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 82572-Methyl-3-buten-2-olHCID 54509253HCID 54509253, compoundHCID 178418339Butyllithium

Product 1

HCID 53853733HCID 53853733, compound

Procedure

To a solution of 2-methyl-3-buten-2-ol (4.1 g, 0.048 mole) in dry ether (10 ml) stirred under dry nitrogen at 5° C. was added a solution of n-butyllithium (19.3 ml, 0.048 mole, 2.5M in hexane). After completion of the addition, ethyl 2-(2-butyl)malonyl chloride (10.0 g, 0.048 mole) was added slowly with stirring, and an additional 10 ml quantity of ether was added. The suspension was stirred for 2 hours with warming to room temperature. The resultant suspension was extracted with water, a saturated ammonium chloride solution, and then water again. The layers were separated and the organic layer dried over magnesium sulphate, filtered, and subjected to reduced pressure distillation. The pale yellow liquid obtained was subjected to fractional distillation. A heart cut of 8.0 g (64.5%), b.p. 69°-71° C. at 0.1 mm, was obtained.

Workup

  1. additionwas added slowly
  2. stirringThe suspension was stirred for 2 hours
  3. extractionThe resultant suspension was extracted with water
  4. customThe layers were separated
  5. dry with materialthe organic layer dried over magnesium sulphate
  6. filtrationfiltered
  7. distillationsubjected to reduced pressure distillation
  8. customThe pale yellow liquid obtained
  9. distillationwas subjected to fractional distillation
  10. customA heart cut of 8.0 g (64.5%), b.p. 69°-71° C. at 0.1 mm, was obtained

Sources & evidence

ORD record
ord-5289966424d643aaa08f2c822f3a9e65
Source dataset
uspto-grants-1984_09
Patent number
US04470421

Reaction notes

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