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

HRID 2211745

반응식

HRID 2211745 반응식
[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

참가 물질

7

반응물 4

HCID 8058HexaneHCID 219613102-Bromo-3,5,6-trimethylanisoleHCID 219613551-Benzyl-4-(4-isopropylbenzoyl)piperidineHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7a0d3804032f4375ac72b49972c02bc8
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101867B2

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