2-(4-bromophenyl)-3,6-dihydro-2H-pyran → 2-(4-Bromophenyl)oxolane

HRID 1054887Notes

Reaction equation

HRID 1054887 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH:12]=[CH:11]C[O:9]2)=[CH:4][CH:3]=1.[H][H]>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][O:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 866988612-(4-bromophenyl)-3,6-dihydro-2H-pyranHCID 178418361HCID 178418361, compound

Product 1

HCID 146531812-(4-Bromophenyl)oxolaneYield 37.6%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 21863594Toluene ethanolSolvent

Procedure

A solution of 2-(4-bromophenyl)-3,6-dihydro-2H-pyran (140 mg, 0.586 mmol) in toluene/ethanol (10 mL, v/v=1/1) was charged into a hydrogenation Parr bottle followed by tris(triphenylphosphine)rhodium(I) chloride (55 mg, 0.0586 mmol). The mixture was set up for 45 psi of hydrogen at 80° C. overnight. The mixture was filtered through celite and the filtrate was concentrated. The residue was purified by silica gel chromatography to give the title compound (50 mg, 35%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.46 (d, 2H) 7.23 (d, 2H) 4.29 (d, 1H) 4.13 (m, 1H) 3.60 (t, 1H) 1.95 (m, 1H) 1.81 (d, 1H) 1.60 (m, 3H) 1.27 (m, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-89e469897dea4abd8edeb675d65ac829
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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