Furan-3-boronic acid → HCID 25234470, compound

HRID 1675507Notes

Reaction equation

HRID 1675507 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[O:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1>>[O:9]1[CH:13]=[CH:12][C:11]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)=[CH:10]1

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 25234470HCID 25234470, compoundYield 16%

Procedure

Synthesized from 3-bromocyclohex-2-enone and furan-3-boronic acid according to the general procedure described for the Suzuki coupling. Purification by silica gel column chromatography using gradient elution (0 to 30% ether/hexanes) yielded the product (13 mg, 16%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.70 (s, 1H), 7.44 (t, J=1.9 Hz, 1H), 6.59 (t, J=1.1 Hz, 1H), 6.24 (s, 1H), 2.63 (td, J=5.7, 1.1 Hz, 2H), 2.46 (t, J=6.3 Hz, 2H), 2.11 (quintet, J=6.3 Hz, 2H). 13C (75 MHz, CDCl3): 200.1, 152.0, 144.6, 142.4, 126.0, 123.3, 107.6, 37.6, 27.5, 22.7. HRMS (LCT Electrospray): mass calcd for (C10H10O2+Na) m/z 185.0578; measured [M+Na]+: m/z 185.0574.

Workup

  1. customPurification by silica gel column chromatography
  2. washelution (0 to 30% ether/hexanes)

Sources & evidence

ORD record
ord-5140432b185f48be98544060bbc2e43f
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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