1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol → HCID 21192141, compound

HRID 1067152Notes

Reaction equation

HRID 1067152 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)(O)[C:27]#[CH:28])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:3]3[CH:28]=[CH:27][C:26]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)([C:23]4[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=4)[O:1][C:2]=32)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 46444481,1-bis(4-methoxyphenyl)prop-2-yn-1-olHCID 21192140Methyl 4-hydroxy-6-methoxy-2-naphthalenecarboxylate

Product 1

HCID 21192141HCID 21192141, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 4-hydroxy-6-methoxy-2-naphthoate (1.0 g, 4.3 mmol) and 1,1-di(4-methoxyphenyl)prop-2-yn-1-ol (1.16 g, 4.3 mmol) in toluene (45 cm3) containing acidic alumina (Brockmann 1), (4.0 g) was refluxed for 45 minutes. The cooled solution was filtered and the alumina was washed well with EtOAc (200 cm3). The organic filtrate was washed with aqueous sodium hydroxide (2M, 2×50 cm3) and water (100 cm3). Removal of the dried (Na2SO4) EtOAc gave an oil which was flash chromatographed over silica using 25% EtOAc in hexane as the eluent to afford a pale yellow solid. Recrystallisation from EtOAc/hexane gave methyl 9-methoxy-2,2-bis(4-methoxyphenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate (yield=0.79 g, theoretical yield=2.08 g 38%, m.p. 162.5-164.0° C. (uncorrected)).

Workup

  1. temperaturewas refluxed for 45 minutes
  2. filtrationThe cooled solution was filtered
  3. washthe alumina was washed well with EtOAc (200 cm3)
  4. washThe organic filtrate was washed with aqueous sodium hydroxide (2M, 2×50 cm3) and water (100 cm3)
  5. customRemoval of the
  6. dry with materialdried (Na2SO4) EtOAc
  7. customgave an oil which
  8. customchromatographed over silica using 25% EtOAc in hexane as the eluent
  9. customto afford a pale yellow solid
  10. customRecrystallisation from EtOAc/hexane

Sources & evidence

ORD record
ord-130a949a20f24955964c695f7ca48b75
Source dataset
uspto-grants-2001_06
Patent number
US06248264B1

Reaction notes

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