Diethyl Ether → HCID 59212660, compound

HRID 2387469Notes

Reaction equation

HRID 2387469 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]([F:25])([F:24])[C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[CH:19][CH:20]2[OH:23])=[CH:16][CH:15]=1.CCOCC>C(Cl)Cl>[F:12][C:13]([F:24])([F:25])[C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[CH:19][C:20]2=[O:23])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 592126236-(trifluoromethyl)-1H-inden-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 59212660HCID 59212660, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridinium chlorochromate (1.08 g, 5.0 mmol) in methylene chloride (15 mL) was added dropwise a solution of 6-(trifluoromethyl)-1H-inden-1-ol (500 mg, 2.498 mmol) in methylene chloride (10 mL). After being stirred for 14 h, ether (30 mL) was added, and the reaction mixture was filtered through silica gel. The filtrate was concentrated in vacuo. The crude material was chromatographed (10:1 hexane/EtOAc) to afford 200 mg (40%) of the product. LC-MS [M+1]=199.2.

Workup

  1. filtrationthe reaction mixture was filtered through silica gel
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe crude material was chromatographed (10:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-f028f1e97feb42419e2354fb3d4d8757
Source dataset
uspto-grants-2012_09
Patent number
US08268826B2

Reaction notes

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