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

HRID 2198778

반응식

HRID 2198778 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-047418f600a44e3cb4e3cdbc8afef10e
출처 데이터셋
uspto-grants-1982_11
특허 번호
US04359467

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