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

HRID 1066305ノート

反応式

HRID 1066305 の反応式
[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>C(Cl)Cl>[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]

参加物

6

反応物 4

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

生成物 1

HCID 22621946ETHYL alpha-METHYL-3-PYRIDYLACETIC ACID収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 CH2Cl2 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).

後処理

  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

出典と根拠

ORDレコード
ord-e381ca120c5b4c63bea5fdcf91c6a04c
出典データセット
uspto-grants-2001_06
特許番号
US06242458B1

反応ノート

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