Sodium Hydroxide → 2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzaldehyde

HRID 2075056ノート

反応式

HRID 2075056 の反応式
[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[CH2:18][OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][C:9]=2[CH:18]=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 58968734(2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)phenyl)methanol

生成物 1

HCID 589686992-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzaldehyde収率 96.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)phenyl)methanol (113.1 mg, 0.37 mmol) in methylene chloride (2 mL) at room temperature was added Dess-Martin periodinane reagent (175 mg, 0.41 mmol). The mixture was stirred at room temperature for 1 hour. 1N NaOH was added and the mixture was extracted with ethyl acetate. Combined organic layers were washed with 1N NaOH, brine, dried over sodium sulfate and concentrated in vacuo to yield the title compound (107.2 mg, 95%). 1H NMR (400 MHz, CDCl3) δ ppm 1.07-1.18 (m, 4H) 1.36 (d, J=5.81 Hz, 1H) 1.53-1.69 (m, 4H) 1.71-1.76 (m, J=2.49 Hz, 1H) 1.83-1.90 (m, 1H) 3.22 (s, 3H) 4.73 (d, J=6.22 Hz, 1H) 7.66 (d, J=8.30 Hz, 1H) 7.81 (dd, J=8.30, 1.66 Hz, 1H) 8.14 (s, 1H) 10.41 (s, 1H).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washCombined organic layers were washed with 1N NaOH, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-87eefe1a8ffd4753857f7efe62b895df
出典データセット
uspto-grants-2011_04
特許番号
US07919506B2

反応ノート

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