HCID 12838740, compound → HCID 68709642, compound

HRID 1875368Notes

Reaction equation

[OH:1][C:2]1[C:11]2[CH:12]=[CH:13][O:14][C:10]=2[C:9]([OH:15])=[C:8]2[C:3]=1[C:4](=[O:17])[CH:5]=[C:6](C)[O:7]2.Br[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][CH2:19][O:15][C:9]2[C:10]3[O:14][CH:13]=[CH:12][C:11]=3[C:2]([OH:1])=[C:3]3[C:8]=2[O:7][CH:6]=[CH:5][C:4]3=[O:17])=[CH:23][CH:24]=1

Participants

Reactant 2

HCID 12838740HCID 12838740, compound

HCID 147371331-(3-Bromopropyl)-4-fluorobenzene

Product 1

HCID 68709642HCID 68709642, compound

Procedure

4,9-Dihydroxy-7-methyl-5H-furo[3,2-g]chromen-5-one was reacted with 1-bromo-3-(4-fluorophenyl)propane according to General Procedure A to give 9-(3-[4-fluorophenyl]propoxy)-4-hydroxy-5H-furo[3,2-g]chromen-5-one, that was further reacted according to General Procedure G step 1-3, to provide the title compound in 22% yield (over 4 steps). 1H NMR (300 MHz, CDCl3): δ 2.04-2.14 (m, 2H), 2.53 (s, 3H, CH3), 2.63 (s, 3H, CH3), 2.83 (t, J=7.8, 2H), 4.34 (t, J=6.3, 2H), 6.73 (d, J=2.1, 1H), 6.94 (t J=8.7 Hz, 2H), 7.13-7.18 (m, 2H), 7.50 (d, J=2.1 Hz, 1H), 8.98 (s, 1H, OH). MS (ES) m/z: 342.9 (M+H+).

Sources & evidence

ORD record: ord-5179d53e2ce04a86a0b36c7bae79e2f7
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309545B2

Reaction notes

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