Ethyl Acetate → 4-Formyl-2-methoxy-5-methylphenyl trifluoromethanesulfonate

HRID 1187006ノート

反応式

HRID 1187006 の反応式
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]([F:35])([F:34])[S:21](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:23])=[O:22].CCOC(C)=O>CN(C=O)C>[F:19][C:20]([F:35])([F:34])[S:21]([O:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[O:10][CH3:11])(=[O:23])=[O:22]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5498704-Nitrophenyl trifluoromethanesulfonateHCID 234242834-Hydroxy-5-methoxy-2-methylbenzaldehyde

生成物 1

HCID 866473084-Formyl-2-methoxy-5-methylphenyl trifluoromethanesulfonate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-Hydroxy-5-methoxy-2-methylbenzaldehyde (20.0 g, 122 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (33.3 g, 241 mmol) and 4-nitrophenyl trifluoromethanesulfonate (49.0 g, 181 mmol) and the reaction mixture was stirred for 8 hr. EtOAc (600 mL) was added to the reaction mixture and the organic layer was washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7) to provide 4-Formyl-2-methoxy-5-methylphenyl trifluoromethanesulfonate. 1H NMR (CDCl3, 500 MHz) δ 10.34 (s, 1H), 7.53 (s, 1H), 7.16 (s, 1H), 3.99 (s, 3H), 2.67 (s, 3H); LC/MS: (IE, m/z) [M+1]+=298.97; tR=3.44 min.

後処理

  1. washthe organic layer was washed three times with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7)

出典と根拠

ORDレコード
ord-c4698b5df6764da8bcf876a01c32a8d4
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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