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

HRID 604663ノート

反応式

HRID 604663 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6df4557615804591b33a204f8a249f4c
出典データセット
uspto-grants-2011_03
特許番号
US07910592B2

反応ノート

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