7-fluoro-2H-chromene → 7-Fluorochroman

HRID 1912621Notes

Reaction equation

HRID 1912621 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH2:8][O:9]2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 224047387-fluoro-2H-chromene

Product 1

HCID 224048067-Fluorochroman

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7-Fluoro-2H-chromene (4.17 g, 27.8 mmol) and Pd/C (500 mg, 10 wt %) in ethyl acetate (70 mL) was stirred under hydrogen at 60 psi for 6 hours. The reaction was filtered through a pad of Celite™ and concentrated under reduced pressure to give the desired product as the major regioisomer in a 3:1 mixture of regioisomers as a yellow oil. This material was used without further purification in the next step. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=6.97 (t, J=7.5 Hz, 1 H), 6.57-6.49 (m, 1 H), 4.21-4.16 (m, 2 H), 2.76 (t, J=6.4 Hz, 2 H), 2.05-1.98 (m, 2 H); LCMS (m/z) ES+=152 (M+).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite™
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3562a913ad724000a05840cbdf793816
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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