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

HRID 2389323

반응식

HRID 2389323 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6c2c0f1bedca4ae4af36eb8e4e219608
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273745B2

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