Triethylamine → Cyano(6-phenoxy-2-pyridyl)methyl 2-(2-naphthyl)-3-methylbutanoate

HRID 27699Notes

Reaction equation

HRID 27699 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13].C(N(CC)CC)C.[C:25]([CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:30]=1)O)#[N:26]>CCOCC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([O:14][CH:27]([C:25]#[N:26])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:30]=1)=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12884337Cyano(6-phenoxy-2-pyridyl)methanolHCID 139522283-Methyl-2-(naphthalen-2-yl)butanoic acid

Product 1

HCID 54346705Cyano(6-phenoxy-2-pyridyl)methyl 2-(2-naphthyl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the acid chloride of 2-(2-naphthyl)-3-methylbutanoic acid (2.5 mmol) in ether is added 1.3 ml of triethylamine followed by the cyano(6-phenoxy-2-pyridyl)methanol in 5 ml of ether, from part A above, over about 2 minutes. The reaction mixture is stirred for about 18 hours and then quenched with saturated aqueous sodium bicarbonate. The organic phase is washed with aqueous sodium bicarbonate, water and brine, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a circular chromatograph eluting with 20% ether/hexane to give cyano(6-phenoxy-2-pyridyl)methyl 2-(2-naphthyl)-3-methylbutanoate, MS m/e 436 (M+).

Workup

  1. customover about 2 minutes
  2. customquenched with saturated aqueous sodium bicarbonate
  3. washThe organic phase is washed with aqueous sodium bicarbonate, water and brine
  4. dry with materialdried over calcium sulfate and solvent
  5. customevaporated
  6. customThe crude product is chromatographed on a circular chromatograph
  7. washeluting with 20% ether/hexane

Sources & evidence

ORD record
ord-8dbca162771e40b0b5a7f74f9d9780a1
Source dataset
uspto-grants-1980_09
Patent number
US04223033

Reaction notes

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