Cesium carbonate → methyl(2S)-2-[4-fluoro-3-(3-hydroxypropyl)phenoxy]propanoate

HRID 2389323

反応式

HRID 2389323 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][OH:12].Cl[C@H:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C@@H:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][OH:12]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 149593Methyl 2-chloropropanoate, (R)-HCID 685363254-Fluoro-3-(3-hydroxypropyl)phenol

生成物 1

HCID 68533499methyl(2S)-2-[4-fluoro-3-(3-hydroxypropyl)phenoxy]propanoate収率 66.8%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 4-fluoro-3-(3-hydroxypropyl)phenol (1.5 g), methyl (2R)-2-chloropropanoate (1.30 g) in DMSO (7.5 mL) was added Cs2CO3 (3.45 g) at ambient temperature. The mixture was stirred at 60° C. for 3 hours. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc (50 mL) and washed successively with water (30 mL) two times and brine (30 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=4:1-2:1) to give methyl(2S)-2-[4-fluoro-3-(3-hydroxypropyl)phenoxy]propanoate (1.51 g) as a colorless oil.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. washwashed successively with water (30 mL) two times and brine (30 mL)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give crude oil
  7. customThe crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=4:1-2:1)

出典と根拠

ORDレコード
ord-6c2c0f1bedca4ae4af36eb8e4e219608
出典データセット
uspto-grants-2012_09
特許番号
US08273745B2

関連ノート

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