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

HRID 2075056노트

반응식

HRID 2075056 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-87eefe1a8ffd4753857f7efe62b895df
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919506B2

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