Diethyl Ether → HCID 59212660, compound

HRID 1191948Notes

Reaction equation

HRID 1191948 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-d65e82bdac754ec691ef7b47ca956a0d
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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