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

HRID 17062ノート

反応式

HRID 17062 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ee6070e3ae2143b68083edc55242dab9
出典データセット
uspto-grants-2010_06
特許番号
US07737295B2

反応ノート

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