Diethyl Ether → HCID 20651890, compound

HRID 1976216Notes

Reaction equation

HRID 1976216 reaction equation
[H-].[Na+].Cl[C:4]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH2:5]1.CCO[CH2:21][CH3:22].[CH3:23][N:24]([CH:26]=[O:27])[CH3:25]>>[CH3:23][N:24]([CH3:25])[C:26]([C:9]1[C:21]2[C:22](=[CH:17][CH:12]=[CH:13][C:14]=2[O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:6]=2)[CH:6]=[CH:5][CH:4]=1)=[O:27]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 70226334HCID 70226334, compound

Product 1

HCID 20651890HCID 20651890, compound

Procedure

To a solution of 8-hydroxynaphthalene-1-(N,N-dimethyl)carboxamide (68 mg, 0.32 mmol) in dry DMF (4 mL) was added sodium hydride (8 mg, 0.35 mmol, 1.1 eq). The sodium hydride was added as 14 mg of a 60% dispersion in mineral oil that had been previously washed with 3×heptane portions under an inert atmosphere. The mixture was stirred for 30 minutes at room temperature and 1-chloro-(4-biphenyl)methanol (71 mg, 0.35 mmol, 1.1 eq) was added. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured onto ice/water (100 mL), and the aqueous-DMF layer was extracted into ethyl acetate portions. The combined organic layers were washed (brine), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, eluant:ethyl acetate/heptane mixtures) to give the desired ether (yield: 99 mg, 0.25 mmol, 79%);

Workup

  1. washhad been previously washed with 3×heptane portions under an inert atmosphere
  2. stirringThe resulting mixture was stirred at room temperature overnight
  3. additionThe reaction mixture was poured onto ice/water (100 mL)
  4. extractionthe aqueous-DMF layer was extracted into ethyl acetate portions
  5. washThe combined organic layers were washed (brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (silica gel, eluant:ethyl acetate/heptane mixtures)

Sources & evidence

ORD record
ord-eaaec6a40b634bd9bdb9e4e8ea407711
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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