Water → 1-(4-Isopropylphenyl)-1-(2-methoxyphenyl)-2-methylpropan-1-ol

HRID 2376295

반응식

HRID 2376295 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1)([CH3:17])[CH3:16].O>C1COCC1>[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])([OH:28])[CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1)([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 113582-BromoanisoleHCID 42512442-(4-Isobutyrylphenyl)propaneHCID 178418339Butyllithium

생성물 1

HCID 231138311-(4-Isopropylphenyl)-1-(2-methoxyphenyl)-2-methylpropan-1-ol수율 43%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-bromoanisole (5.0 g, 26.7 mmol) in THF (50 mL) was added n-butyllithium (1.6 M, 18 mL, 29 mmol) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction solution was added 1-(4-isopropylphenyl)-2-methylpropan-1-one (5.70 g, 30.0 mmol), and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture which was extracted with ethyl acetate, and the combined organic layer was washed with water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 3.4 g (yield 43%) of the title compound. Melting point: 85-86° C. (methanol).

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washthe combined organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

출처 및 근거

ORD 기록
ord-fee60b443379464bac99173649cfa70f
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465815B2

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