Methyl iodide → ETHYL alpha-METHYL-3-PYRIDYLACETIC ACID

HRID 861721노트

반응식

HRID 861721 반응식
[CH2:1]([CH:3]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[C:4]([OH:6])=[O:5])[CH3:2].[CH:13]([N-]C(C)C)(C)C.[Li+].C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.CI.ClCl>>[CH2:1]([C:3]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)([CH3:13])[C:4]([OH:6])=[O:5])[CH3:2]

참가 물질

6

반응물 5

HCID 6328Methyl iodideHCID 24526ChlorineHCID 2724682Lithium diisopropylamideHCID 179099082-(Pyridin-3-yl)butanoic acidHCID 22742125Tetrahydrofuran heptane ethylbenzol

생성물 1

HCID 22621946ETHYL alpha-METHYL-3-PYRIDYLACETIC ACID수율 30%

실험 절차

To ethyl 3-pyridylacetic acid (10.86 grams) (65.7 mmoles) was added a 2.0M solution of lithium diisopropylamide in THF/heptane/ethyl benzene (32.87 ml.) (65.8 mmoles) at -30° C. The semi-solid mixture was agitated and sonicated for 1 hour. The mixture was allowed to remain at 25° C. for 1 hour, whereupon methyl iodide (4.09 ml.) (65.7 mmoles) was added. After 1 hour at 25° C. the mixture was taken up in CH2 Cl2 and washed with saturated aqueous sodium bicarbonate and water. The CH2Cl2 was dried (magnesium sulphate), filtered and evaporated to dryness. The residue was chromatographed on silica gel using 10% EtOAc in hexane as the eluant to give the title compound (Yield: 3.48 grams, 30%, MH+ 180).

후처리

  1. customsonicated for 1 hour
  2. additionwas added
  3. washwashed with saturated aqueous sodium bicarbonate and water
  4. dry with materialThe CH2Cl2 was dried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel using 10% EtOAc in hexane as the eluant

출처 및 근거

ORD 기록
ord-4376185395d4406ba9849763f6eba918
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714609

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