Sodium Hydroxide → 3-(Methylthio)-5-(trifluoromethyl)benzaldehyde

HRID 17062노트

반응식

HRID 17062 반응식
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH2:13][OH:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[CH:13]=[O:14]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 68687257[3-(Methylthio)-5-(trifluoromethyl)phenyl]methanol

생성물 1

HCID 593438793-(Methylthio)-5-(trifluoromethyl)benzaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of [3-(methylthio)-5-(trifluoromethyl)phenyl]methanol (200 mg, 0.99 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and then Dess-Martin periodinane (573 mg, 1.35 mmol) was added. The reaction was slowly warmed to room temperature. After stirring at room temperature for twenty minutes, the reaction was poured into 1N NaOH (25 mL). The mixture was extracted with EtOAc (75 mL). The organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 1% to 10% EtOAc/hexanes afforded 3-(methylthio)-5-(trifluoromethyl)benzaldehyde. Rf=0.55 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 10.02 (s, 1H), 7.87 (s, 1H), 7.84 (s, 1H), 7.68 (s, 1H), 2.58 (s, 3H).

후처리

  1. extractionThe mixture was extracted with EtOAc (75 mL)
  2. washThe organic extracts were washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 1% to 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-ee6070e3ae2143b68083edc55242dab9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737295B2

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