1-Naphthaldehyde → HCID 86752821, compound

HRID 964718Notes

Reaction equation

HRID 964718 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]([NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.C([Li])CCC.[C:23]1([CH:33]=O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.[O:35]1CCCC1>>[OH:35][C:23]1([CH2:33][C:14]2[CH:15]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:4]=[CH:5][C:6]=2[NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH2:24]1

Participants

5

Reactant 4

HCID 61951-NaphthaldehydeHCID 8028Tetrahydrofuran2×HCID 2774289N-(4-(trifluoromethyl)phenyl)pivalamideHCID 178418339Butyllithium

Product 1

HCID 86752821HCID 86752821, compoundYield 52%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4'-trifluoromethyl-2,2-dimethylpropionanilide (37 g, 0.15 mol) in anhydrous tetrahydrofuran (400 ml) cooled to 0° C. under nitrogen was added slowly a solution of n-butyllithium (160 mL of 2.5M solution in hexane, 0.4 mol). The reaction mixture was stirred at 0° C. for 2 hr, then a solution of 1-naphthaldehyde (40.7 ml, 0.3 mol) in tetrahydrofuran (50 ml) was slowly added. The resulting solution was stirred at room temperature overnight, quenched with water, diluted with ethyl acetate and separated. The aqueous phase was extracted with ethyl acetate (2×) and the combined ethyl acetate extracts were washed with water and brine, dried (anhydrous sodium sulfate) and concentrated. in vacuo to an oil (74 g). The crude product was chromatographed on 2 kg silica gel, eluting with 8:2 hexane/ethyl acetate to yield the title compound as a tan solid (31 g, 52% yield).

Workup

  1. stirringThe resulting solution was stirred at room temperature overnight
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. customseparated
  5. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  6. washthe combined ethyl acetate extracts were washed with water and brine
  7. dry with materialdried (anhydrous sodium sulfate)
  8. concentrationconcentrated
  9. customThe crude product was chromatographed on 2 kg silica gel
  10. washeluting with 8:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-2988b0085fbb45be84fbc2cd0adc25c8
Source dataset
uspto-grants-1998_06
Patent number
US05770594

Reaction notes

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