1-[5-(Trifluoromethyl)-2-vinylphenyl]prop-2-en-1-ol → 6-(trifluoromethyl)-1H-inden-1-ol

HRID 2178791Notes

Reaction equation

HRID 2178791 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([CH:13]=[CH2:14])=[C:7]([CH:9]([OH:12])C=C)[CH:8]=1>C(Cl)Cl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:8]=[C:7]2[C:6]([CH:13]=[CH:14][CH:9]2[OH:12])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 592126561-[5-(Trifluoromethyl)-2-vinylphenyl]prop-2-en-1-ol

Product 1

HCID 592126236-(trifluoromethyl)-1H-inden-1-olYield 68.8%

Reagents, catalysts & solvents 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the 1-[5-(trifluoromethyl)-2-vinylphenyl]prop-2-en-1-ol (462 mg, 2.02 mmol) in methylene chloride (20 mL) under nitrogen was added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (70 mg, 0.08 mmol). The dark mixture was stirred at 25° C. for 30 min and concentrated. The residue was purified by flash chromatography to give the desired compound (278.1 mg, 68%). LC-MS [M+1]=279.2.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3655b6da224044ca8949d3c5a40bf97a
Source dataset
uspto-grants-2015_06
Patent number
US09067921B2

Reaction notes

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