HCID 68379780, compound → HCID 68380276, compound

HRID 2178670Notes

Reaction equation

HRID 2178670 reaction equation
[F:1][C:2]1([F:21])[CH2:5][CH:4]([C:6]2[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=2[O:13]CC2C=CC=CC=2)[CH2:3]1>C(O)C.[Pd]>[F:21][C:2]1([F:1])[CH2:5][CH:4]([C:6]2[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=2[OH:13])[CH2:3]1

Participants

4

Reactant 1

HCID 68379780HCID 68379780, compound

Product 1

HCID 68380276HCID 68380276, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 2-(3,3-difluorocyclobutyl)-4-fluorophenyl ether (C20) (60 mg, 0.20 mmol) in ethanol (15 mL) was treated with palladium (50 mg, 0.47 mmol) and shaken on a Parr hydrogenator (50 psi) at room temperature for 2 hours. The mixture was filtered through Celite and concentrated in vacuo to afford the title compound as a yellow oil. Yield: 20 mg, 0.065 mmol, 100%. GCMS m/z 202 (M+). 1H NMR (400 MHz, CDCl3) δ 2.60-2.78 (m, 2H), 2.92-3.07 (m, 2H), 3.46-3.58 (m, 1H), 6.61-6.95 (m, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfb17291ba41414b8c6473878cc3c4f4
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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