Phenylacetone → 4-(4-Methylphenyl)-3-phenylbutan-2-one

HRID 30383

반응식

HRID 30383 반응식
[C:1]1([CH2:7][C:8]([CH3:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:9])[CH3:10])=[CH:17][CH:16]=1

참가 물질

7

반응물 3

HCID 7678PhenylacetoneHCID 77224-Methylbenzyl chlorideHCID 14797Potassium Hydroxide

생성물 1

HCID 126157934-(4-Methylphenyl)-3-phenylbutan-2-one

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

1-Phenylacetone (200 mg, 1.49 mmol) was mixed with powdered potassium hydroxide (167 mg, 2.98 mmol) and tetra-n-butylammonium bromide (1 mol %, 5 mg) in a flask without solvent. This mixture was stirred at room temperature for 90 min. before the addition of 1-(chloromethyl)4-methylbenzene (198 μl, 1.49 mmol). The reaction mixture was then stirred overnight before diluting with water and CH2Cl2. The aqueous layer was separated and neutralized to pH 7 with 2N hydrochloric acid and extracted again into CH2Cl2. The combined organic washes were dried with MgSO4 and concentrated. The crude material was purified by column chromatography on silica gel eluting from 0-10% EtOAc/hexane to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.35 (t, J=7.0 Hz, 2H), 7.29 (t, J=7.4 Hz, 1H), 7.23 (d, J=7.1 Hz, 2H), 7.05 (d, 7.8 Hz, 2H), 6.98 (d, J=7.8 Hz, 2H), 3.94 (t, J=7.3 Hz, 1H), 3.43 (dd, J=13.9, 7.5 Hz, 1H), 2.91 (dd, J=14, 7.1 Hz, 1H), 2.32 (s, 3H), 2.08 (s, 3H). LC-MS: m/e 239 (M+H)+ (3.61 min).

후처리

  1. customThe aqueous layer was separated
  2. extractionextracted again into CH2Cl2
  3. dry with materialThe combined organic washes were dried with MgSO4
  4. concentrationconcentrated
  5. customThe crude material was purified by column chromatography on silica gel eluting from 0-10% EtOAc/hexane

출처 및 근거

ORD 기록
ord-b062a33c4049454aad6798b6b79f78f1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423067B2

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