HCID 70654827, compound → HCID 69726087, compound

HRID 705198Notes

Reaction equation

HRID 705198 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][CH2:11][O:12][CH2:13][CH:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 70654827HCID 70654827, compound

Product 1

HCID 69726087HCID 69726087, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(3,5-difluorophenyl)-3,6-dihydro-2H-pyran (1.0 equiv.) in methanol (0.2 M) was added 10% Pd/C (0.05 equiv.). The reaction was placed under an atmosphere of hydrogen and stirred for 18 hours. Upon completion, the solution was filtered over a pad of Celite, the pad was washed with DCM, the filtrate was concentrated in vacuo to give 4-(3,5-difluorophenyl)tetrahydro-2H-pyran in 71% yield. 1H NMR (400 MHz, <cdcl3>) δ ppm 1.76 (br. s., 4 H), 2.75 (br. s., 1 H), 3.50 (br. s., 2 H), 4.08 (d, J=9.78 Hz, 2 H), 6.56-6.94 (m, 3 H). cl Synthesis of 2-(2,6-difluoro-4-(tetrahydro-2H-pyran-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Workup

  1. filtrationUpon completion, the solution was filtered over a pad of Celite
  2. washthe pad was washed with DCM
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a986640fae2b456b86da9a3c1edd76e2
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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