Cesium carbonate → ethyl {(1S)-5-[3-(4-cyano-2-propylphenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate

HRID 2235887노트

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HRID 2235887 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].[CH2:13]([O:15][C:16](=[O:32])[CH2:17][C@H:18]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH2:28][CH2:29][CH2:30]Br)=[CH:24][CH:25]=2)[CH2:20][CH2:19]1)[CH3:14].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:30][CH2:29][CH2:28][O:27][C:23]2[CH:22]=[C:21]3[C:26](=[CH:25][CH:24]=2)[C@H:18]([CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:32])[CH2:19][CH2:20]3)=[C:3]([CH2:10][CH2:11][CH3:12])[CH:4]=1)#[N:7]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 139876694-hydroxy-3-propylBenzonitrileHCID 16110497ethyl[(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate

생성물 1

HCID 16110506ethyl {(1S)-5-[3-(4-cyano-2-propylphenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate수율 66%

시약·촉매·용매 2

HCID 962Water촉매HCID 6228Dimethylformamide용매

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온도
40 °C

실험 절차

To a mixture of 4-hydroxy-3-propylbenzonitrile (Example 29, 0.5 g, 3.1 mmol), ethyl [(1S-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 45, 1.1 g, 3.1 mmol) and Cs2CO3 (1.2 g, 3.7 mmol) in DMF (10 mL) was added water (6 drops). The reaction mixture was stirred at 40° C. for 16 h and then concentrated under reduced pressure. The residue was taken up in water and extracted with EtOAc (2×). The combined organic phases were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/Hexane (v/v) 1:20) gave 0.86 g (66%) of the title compound as a light yellow oil. LC-MS: RT=4.12 min; (M+H)+ 422.0.

후처리

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel flash chromatography (EtOAc/Hexane (v/v) 1:20)

출처 및 근거

ORD 기록
ord-683526fb42e84ce4bdcbefb2a3378f74
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714004B2

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