Sodium Chloride → Methyl 2,2,5-trimethyl-4-hexenoate

HRID 894641

反応式

HRID 894641 の反応式
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].[CH3:9][O:10][C:11](=[O:15])C(C)C.Br[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20].[Cl-].[Na+]>CCCCCC.CS(C)=O.O1CCCC1>[CH3:9][O:10][C:11](=[O:15])[C:5]([CH3:6])([CH3:7])[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20]

参加物

8

反応物 4

HCID 5234Sodium ChlorideHCID 11039Methyl isobutyrateHCID 700922-Butene, 1-bromo-3-methyl-HCID 2724682Lithium diisopropylamide

生成物 1

HCID 550269Methyl 2,2,5-trimethyl-4-hexenoate

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

300 g. of a 10% solution of lithium diisopropylamide in hexane was introduced into 90 ml. of absolute tetrahydrofuran, cooled to 0°, and combined dropwise under agitation with a solution of 28 g. of isobutyric acid methyl ester in 150 ml. of absolute tetrahydrofuran. The reaction solution was stirred for one hour at 0°, then cooled to -40° and subsequently added to a solution of 58 g. of 4-bromo-2-methyl-2-butene (dimethylallyl bromide) in 60 ml. of absolute dimethyl sulfoxide, maintained at -20°. While allowing the temperature of the solution to rise to room temperature, the solution was stirred for 6 hours and then combined with saturated sodium chloride solution. The organic phase was separated, the aqueous phase was extracted five times with respectively 200 ml. of a 1/1 mixture of ether and hexane. The combined organic phases were washed neutral with 0.5 N hydrochloric acid and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated on a forced circulation evaporator. The residue was distilled under vacuum, thus obtaining 20.7 g. of the title compound, b.p. (13 mm.) 74°.

後処理

  1. temperaturecooled to -40°
  2. additionsubsequently added to a solution of 58 g
  3. customto rise to room temperature
  4. stirringthe solution was stirred for 6 hours
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted five times with respectively 200 ml
  7. additionof a 1/1 mixture of ether and hexane
  8. washThe combined organic phases were washed neutral with 0.5 N hydrochloric acid and saturated sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated on a forced circulation evaporator
  11. distillationThe residue was distilled under vacuum
  12. customthus obtaining 20.7 g

出典と根拠

ORDレコード
ord-6f7a2a492a3440fbbd9841ef1bb25325
出典データセット
uspto-grants-1981_08
特許番号
US04284646

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