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

HRID 1187006노트

반응식

HRID 1187006 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c4698b5df6764da8bcf876a01c32a8d4
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673920B2

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