Diethyl Ether → alpha-Methyl-4-(3-pyridylmethyl)benzyl alcohol

HRID 2296052ノート

反応式

HRID 2296052 の反応式
C[Mg]I.COC(=O)/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:11][CH:10]=1.[Cl-].[NH4+].C([O:27]CC)C>O1CCCC1>[CH3:7][CH:8]([OH:27])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl esterHCID 178418373HCID 178418373、化合物

生成物 1

HCID 12904574alpha-Methyl-4-(3-pyridylmethyl)benzyl alcohol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under an atmosphere of nitrogen, 1.5 ml of a 3 M solution of methylmagnesium iodide in diethyl ether were added to a solution of 830 mg of the aldehyde (prepared as described in Reference Example 1) in 20 ml of tetrahydrofuran at -70° C., the mixture was allowed to warm from -70° C. to room temperature over a period of one hour with stirring, poured into a saturated aqueous solution of ammonium chloride, and extracted with diethyl ether. The extract was washed with water, and a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:1) as eluent to give 547 mg of the title compound having the following physical characteristics:

後処理

  1. temperatureto warm from -70° C. to room temperature over a period of one hour
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of cyclohexane and ethyl acetate (1:1) as eluent

出典と根拠

ORDレコード
ord-99406c28668f44dea04881f363c3f66b
出典データセット
uspto-grants-1984_01
特許番号
US04427682

反応ノート

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