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

HRID 1154395

반응식

HRID 1154395 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 0.5N 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 0.5N 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-301298307d8149268a7705977a39851a
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04489092

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