Methanol → Methyl 2-(2-fluoro-4-methoxyphenyl)acetate

HRID 604663노트

반응식

HRID 604663 반응식
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].CO.[Si](C=[N+]=[N-])(C)(C)[CH3:17]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([O:13][CH3:17])=[O:12]

참가 물질

5

반응물 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 193619782-(2-Fluoro-4-methoxyphenyl)acetic acid

생성물 1

HCID 21472203Methyl 2-(2-fluoro-4-methoxyphenyl)acetate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of (2-fluoro-4-methoxyphenyl)acetic acid (500 mg, 2.72 mmol) in toluene (20 mL) was added MeOH (3 mL) and TMS diazomethane (2.04 mL of a 2M solution in hexanes, 4.08 mmol). After 15 min, the reaction was quenched by the addition of HOAc (250 μL). The reaction was diluted with EtOAc (100 mL) and washed with saturated NaHCO3 (2×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered and concentrated. Purification of the residue by flash chromatography (0 to 25% EtOAc/hexanes) afforded methyl (2-fluoro-4-methoxyphenyl)acetate. 1H NMR (500 MHz, CDCl3): δ 7.15 (t, J=8.6 Hz, 1H), 6.62-6.68 (m, 2H), 3.78 (s, 3H), 3.70 (s, 3H), 3.60 (s, 2H).

후처리

  1. customthe reaction was quenched by the addition of HOAc (250 μL)
  2. additionThe reaction was diluted with EtOAc (100 mL)
  3. washwashed with saturated NaHCO3 (2×25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography (0 to 25% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-6df4557615804591b33a204f8a249f4c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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