Toluene → Ethyl 2-(1-nonen-1-yl)-3,3-dimethylcyclopropanecarboxylate

HRID 354696

반응식

HRID 354696 반응식
C([Li])CCC.[Br-].[CH2:7]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH:34]([CH:36]1[C:38]([CH3:40])([CH3:39])[CH:37]1[C:41]([O:43][CH2:44][CH3:45])=[O:42])=O.C1(C)C=CC=CC=1>CCCCCC.O1CCCC1.O>[CH:34]([CH:36]1[C:38]([CH3:40])([CH3:39])[CH:37]1[C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 566079Ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylateHCID 3084855Octyltriphenylphosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 54188881Ethyl 2-(1-nonen-1-yl)-3,3-dimethylcyclopropanecarboxylate수율 57%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

64.5 g of a 15% strength solution of butyl-lithium in n-hexane were added dropwise to a suspension of 68.3 g (0.15 mol) of n-octyl-triphenylphosphonium bromide in 300 ml of absolute tetrahydrofuran at 0°-5° C., with the exclusion of air. After one hour, 25.5 g (0.15 mol) of ethyl 2-formyl-3,3-dimethylcyclopropanecarboxylate were slowly added, and the mixture was further stirred for 18 hours at room temperature. The mixture was shaken after the addition of 400 ml of toluene and 300 ml of water, the water was separated off and the organic phase was washed once again with 200 ml of water. The toluene solution was then dried over sodium sulphate and the solvent was distilled off in vacuo. The residue was stirred with 300 ml of petroleum ether (40°-60° C.), the solution was filtered off from the undissolved triphenylphosphine oxide, and the filtrate was again concentrated by evaporation in vacuo. The residue was distilled in vacuo. 22.6 g (57% of theory) of ethyl 2-(1-nonen-1-yl)-3,3-dimethylcyclopropanecarboxylate with a boiling point of 90° C./0.01 mm Hg were thus obtained.

후처리

  1. stirringThe mixture was shaken
  2. customthe water was separated off
  3. washthe organic phase was washed once again with 200 ml of water
  4. dry with materialThe toluene solution was then dried over sodium sulphate
  5. distillationthe solvent was distilled off in vacuo
  6. stirringThe residue was stirred with 300 ml of petroleum ether (40°-60° C.)
  7. filtrationthe solution was filtered off from the undissolved triphenylphosphine oxide
  8. concentrationthe filtrate was again concentrated by evaporation in vacuo
  9. distillationThe residue was distilled in vacuo

출처 및 근거

ORD 기록
ord-180eb195a3fc49f1b48ad354030375a7
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04376786

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