Diethyl Ether → HCID 59212660, compound

HRID 2178792Notes

Reaction equation

HRID 2178792 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-67288fb05b7b447cb094e9b7594a1b3a
Source dataset
uspto-grants-2015_06
Patent number
US09067921B2

Reaction notes

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