Triethylamine → (6-Phenoxy-2-pyridyl)methyl 2-(2-napthyl)-3-methyl-butanoate

HRID 27698Notes

Reaction equation

HRID 27698 reaction equation
[O:1]([C:8]1[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH:33]([CH:37]([CH3:39])[CH3:38])[C:34](O)=[O:35]>CCOCC>[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH:33]([CH:37]([CH3:39])[CH3:38])[C:34]([O:15][CH2:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:13]=1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 128791556-Phenoxy-2-pyridinemethanolHCID 139522283-Methyl-2-(naphthalen-2-yl)butanoic acid

Product 1

HCID 23341821(6-Phenoxy-2-pyridyl)methyl 2-(2-napthyl)-3-methyl-butanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of (6-phenoxy-2-pyridyl)methanol (0.2 g, 0.99 mmol) and triethylamine (0.14 g, 1.38 mmol) in ether (about 15 ml), under nitrogen, is added by syringe a solution of the acid chloride of 2-(2-naphthyl)-3-methylbutanoic acid (1.5 mmol) in ether. The mixture is stirred for 30 minutes and then quenched with saturated aqueous sodium bicarbonate. The ether phase is washed with aqueous sodium bicarbonate, water and brine and filtered through silica. Evaporation of solvent, followed by thin layer chromatography using a circular chromatograph, eluting with 20% ether/hexane, gives (6-phenoxy-2-pyridyl)methyl 2-(2-napthyl)-3-methyl-butanoate, MS m/e 411(M+).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. washThe ether phase is washed with aqueous sodium bicarbonate, water and brine
  3. filtrationfiltered through silica
  4. customEvaporation of solvent
  5. washeluting with 20% ether/hexane

Sources & evidence

ORD record
ord-21ee06759d834d7491dd59f80584af11
Source dataset
uspto-grants-1980_09
Patent number
US04223033

Reaction notes

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