HCID 55275761, compound → HCID 66604057, compound

HRID 1774584Notes

Reaction equation

[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][C:7](=O)[C:6]=2[C:5]([CH3:13])=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH3:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 8-fluoro-5-methyl-3,4-dihydro-2H-1-benzopyran-4-one (10b) (570 mg, 3.16 mmol) in acetic acid (4 mL) was added to a suspension of zinc dust (2.69 g, 41.1 mmol) in acetic acid (4 mL). The reaction mixture was heated at 100° C. for 5 hours. After cooling to room temperature, the mixture was filtered through a pad of Celite® and successively rinsed with ethyl acetate (10 mL) and toluene (10 mL). The filtrate was concentrated in vacuo to provide 8-fluoro-5-methyl-3,4-dihydro-2H-1-benzopyran (10c) (233 mg, 1.40 mol, 44%) which was used without further purification.

Workup

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered through a pad of Celite®
washsuccessively rinsed with ethyl acetate (10 mL) and toluene (10 mL)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-568e471fd32b436086e3def1f9a1617f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260395B2

Reaction notes

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