Hydrochloric Acid → HCID 68534800, compound

HRID 1992993Notes

Reaction equation

HRID 1992993 reaction equation
[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[Li+].[OH-].Cl>C1COCC1>[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)=[C:4]([O:14][C:15]2[CH:16]=[CH:17][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86616675HCID 86616675, compound

Product 1

HCID 68534800HCID 68534800, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution (2 mL) of ethyl (2E)-3-[4-({3-methyl-6-(methyloxy)-2-[3-(methyloxy)phenyl]-1-naphthalenyl}oxy)phenyl]-2-propenoate (249) (0.030 g, 0.06 mmol, 1 equiv) was treated with 1 M aqueous LiOH (0.260 mL). After 2 h at 50° C., the mixture was acidified with 3M aqueous HCl to pH ca. 1 and extracted with EtOAc (3×5 mL). The pooled organic portions were dried (Na2SO4) and concentrated. Radial chromatography (SiO2, 1 mm plate, 80:20; hexanes/EtOAc) afforded the title compound (250) as a white foam (0.024 g, 85%). 1H NMR (CDCl3, 400 MHz) δ 7.69 (d, J=9.2 Hz, 1H), 7.63 (d, J=15.9 Hz, 1H), 7.55 (s, 1H), 7.27 (d, J=8.3 Hz, 2H), 7.16 (dd, J=7.9, 7.9 Hz, 1H), 7.13 (d, J=2.0 Hz, 1H), 7.03 (dd, J=9.1, 2.2 Hz, 1H), 6.77 (dd, J=8.1, 1.9 Hz, 1H), 6.71 (d, J=7.4 Hz, 1H), 6.64-6.60 (m, 3H), 6.22 (d, J=15.9 Hz, 1H), 3.92 (s, 3H), 3.62 (s, 3H), 2.25 (s, 3H). TLC (98:2; CHCl3/MeOH): Rf=0.05.

Workup

  1. extractionextracted with EtOAc (3×5 mL)
  2. dry with materialThe pooled organic portions were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c24e0a294690402ea8404443dff1635b
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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