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

HRID 1814169ノート

反応式

HRID 1814169 の反応式
[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

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 2331475-Hydroxy-1-indanoneHCID 22280095HCID 22280095、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8267578329884dab8a56778fba1dca1a
出典データセット
uspto-grants-2005_04
特許番号
US06875780B2

反応ノート

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