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

HRID 30383

反応式

HRID 30383 の反応式
[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

参加物

7

反応物 3

HCID 7678PhenylacetoneHCID 77224-Methylbenzyl chlorideHCID 14797Potassium Hydroxide

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b062a33c4049454aad6798b6b79f78f1
出典データセット
uspto-grants-2008_09
特許番号
US07423067B2

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