Diethyl Ether → 5-[4-(4-Trifluoromethyl-benzyloxy)-benzyloxy]-indan-1-one

HRID 1814169노트

반응식

HRID 1814169 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[F:12][C:13]([F:31])([F:30])[C:14]1[CH:29]=[CH:28][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26]Cl)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOCC>C(#N)C.O>[F:12][C:13]([F:30])([F:31])[C:14]1[CH:29]=[CH:28][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][O:1][C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[C:7](=[O:11])[CH2:6][CH2:5]4)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 2331475-Hydroxy-1-indanoneHCID 22280095HCID 22280095, 화합물

생성물 1

HCID 225048095-[4-(4-Trifluoromethyl-benzyloxy)-benzyloxy]-indan-1-one수율 305.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

5-Hydroxyindanone (1.0 g, 1.1 mmol) was dissolved in acetonitrile (40 mL) with 5E (1.8 g, 1.0 mmol) and Cs2CO3 (4.4 g, 2.2 mmol). The reaction mixture was stirred at RT for 3 h. Ether (25 mL) and water were added and the stirring was continued for another 5 min. The layers were separated and the aqueous layer was extracted with ether (2×20 mL). The combined organics was dried over MgSO4 and concentrated to a tan solid. The crude product was purified by column chromatography eluted with EtOAc and hexanes to give the desired product, compound 52A as a tan solid (1.26 g, 50%). MS m/z 413 (M+1). Step 2. Preparation of {5-[4-(4-Trifluoromethyl-benzyloxy)-benzyloxy]-indan-1-yl}-acetic acid ethyl ester (Compound 52B).

후처리

  1. waitthe stirring was continued for another 5 min
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ether (2×20 mL)
  4. dry with materialThe combined organics was dried over MgSO4
  5. concentrationconcentrated to a tan solid
  6. customThe crude product was purified by column chromatography
  7. washeluted with EtOAc and hexanes

출처 및 근거

ORD 기록
ord-8267578329884dab8a56778fba1dca1a
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875780B2

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