beta-Iodonaphthalene → HCID 54723593, compound

HRID 369167Notes

Reaction equation

HRID 369167 reaction equation
[CH2:1]([CH:5]1[O:9][C:8](=[O:10])[C:7]([OH:11])=[C:6]1[OH:12])[CH2:2][C:3]#[CH:4].I[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1.OC1C(=O)OC(CCC#CC2C=CC=CC=2)C=1O>>[OH:11][C:7]1[C:8](=[O:10])[O:9][CH:5]([CH2:1][CH2:2][C:3]#[C:4][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[C:6]=1[OH:12]

Participants

4

Reactant 3

HCID 136412beta-IodonaphthaleneHCID 54703388HCID 54703388, compoundHCID 54723600HCID 54723600, compound

Product 1

HCID 54723593HCID 54723593, compoundYield 78.2%

Procedure

5-(3-Butynyl)-3,4-dihydroxy-2(5H)-furanone (0.17 g, 1.0 mmol) and 300 μL (2.0 mmol) of 2-iodonaphthalene were coupled in an analogous fashion as described for the synthesis of 3,4-dihydroxy-5-[(4-phenyl)-3-butynyl]-2(5H)-furanone. The residue was purified over silica gel using CHCl3 /MeOH/AcOH (96/3/1) as eluant and dried at 0.05 mm Hg at 58° C. for 2 h to provide 230 mg (75%) of 3,4-dihydroxy-5-[4-(2-naphthyl)-3-butynyl]-2(5H)-furanone as a yellow wax: 1H NMR (acetone-d6) δ 8.4-8.3 (m, 1H), 7.96-7.88 (m, 2H), 7.70-7.43 (m, 4H), 4.98 (dd, J=3.4, 8.3 Hz, 1H), 2.82-2.75 (m, 2H), 2.48-2.29 (m, 1H), 2.00-1.85 (m, 1H); Anal Calcd for C18H4 0.5 H2O: C, 71.27; H, 4.98. Found: C, 71.33; H, 4.87.

Workup

  1. customThe residue was purified over silica gel
  2. customdried at 0.05 mm Hg at 58° C. for 2 h

Sources & evidence

ORD record
ord-b23d68c5e5df416cb93857dc4c056647
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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