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

HRID 1814169Notes

Reaction equation

HRID 1814169 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8267578329884dab8a56778fba1dca1a
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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