3-Fluoro-4-hydroxybenzeneacetic acid → Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

HRID 453508

反応式

HRID 453508 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Si](C=[N+]=[N-])(C)(C)[CH3:14]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

参加物

4

反応物 2

HCID 680143-Fluoro-4-hydroxybenzeneacetic acidHCID 167693Trimethylsilyldiazomethane

生成物 1

HCID 10797559Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate収率 64.7%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

2-(3-Fluoro-4-hydroxyphenyl)acetic acid (1.0 g, 5.88 mmol) was diluted with THF:MeOH (3:1) (10 mL) followed by the addition of TMSCHN2 (5.88 ml, 11.8 mmol). After stirring for 1 hour, the reaction was quenched with 2N HCl and diluted with DCM. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified by silica gel chromatography, eluting with hexanes:ethyl acetate (2:1) to yield methyl 2-(3-fluoro-4-hydroxyphenyl)acetate (700 mg, 64.7% yield) as a clear oil.

後処理

  1. customthe reaction was quenched with 2N HCl
  2. additiondiluted with DCM
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by silica gel chromatography
  8. washeluting with hexanes:ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-7e60a6359e424f16becd7cc037e0ee9c
出典データセット
uspto-grants-2013_07
特許番号
US08492437B2

関連ノート

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