Hexane → (1-Benzyl-4-piperidyl)(4-isopropylphenyl)(3,4,6-trimethyl-2-methoxyphenyl)methanol

HRID 272354

反応式

HRID 272354 の反応式
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[CH:6]=[C:5]([CH3:11])[C:4]=1Br.C([Li])CCC.CCCCCC.[CH2:24]([N:31]1[CH2:36][CH2:35][CH:34]([C:37](=[O:47])[C:38]2[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:40][CH:39]=2)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.O>[CH2:24]([N:31]1[CH2:32][CH2:33][CH:34]([C:37]([C:38]2[CH:39]=[CH:40][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:42][CH:43]=2)([C:4]2[C:5]([CH3:11])=[CH:6][C:7]([CH3:10])=[C:8]([CH3:9])[C:3]=2[O:2][CH3:1])[OH:47])[CH2:35][CH2:36]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 219613102-Bromo-3,5,6-trimethylanisoleHCID 21961355HCID 21961355、化合物HCID 178418339Butyllithium

生成物 1

HCID 21961358(1-Benzyl-4-piperidyl)(4-isopropylphenyl)(3,4,6-trimethyl-2-methoxyphenyl)methanol収率 79.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-methoxy-3,4,6-trimethylbromobenzene (15.48 g, 67.56 mmol) in tetrahydrofuran (200 ml), which was kept at −78° C., was added dropwise under an argon atmosphere a solution of n-butyllithium in hexane (1.59 mol/l, 42 ml, 66.78 mmol) and the mixture was stirred for 30 minutes. To this mixture was added dropwise a solution of 1-benzyl-4-(4-isopropylbenzoyl)piperidine (19.81 g, 61.63 mmol) in tetrahydrofuran (50 ml) and the resulting mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The extracts were washed with an aqueous saturated solution of sodium chloride, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain 23.01 g (79% yield) of the title compound. Melting point: 154-156° C.

後処理

  1. customwas kept at −78° C.
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extracts were washed with an aqueous saturated solution of sodium chloride
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-090662d5e9834f41b3eccd87ecbc792a
出典データセット
uspto-grants-2008_11
特許番号
US07456162B2

関連ノート

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