Phenol → 6-[(1E)-1-(4-tert-butylphenyl)-3-phenoxyprop-1-en-1-yl]-3-chloro-2-methoxypyridine

HRID 70699Notes

Reaction equation

HRID 70699 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[N:16]=2)=[CH:12]\[CH2:13][OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:15]2[N:16]=[C:17]([O:22][CH3:23])[C:18]([Cl:21])=[CH:19][CH:20]=2)=[CH:12]\[CH2:13][O:14][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 996PhenolHCID 13831TributylphosphineHCID 58452849(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol

Product 1

HCID 673996546-[(1E)-1-(4-tert-butylphenyl)-3-phenoxyprop-1-en-1-yl]-3-chloro-2-methoxypyridineYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N,N′,N′-Tetramethylazodicarbodiimide (104 mg) was added to a solution of (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol obtained in Reference Example 4-4 (199 mg), phenol (63 mg) and tributylphosphine (189 mg) in tetrahydrofuran (4 mL) under ice-cooling, and the mixture was stirred at room temperature for 20 hours. The solvent was evaporated from the reaction solution under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to give 6-[(1E)-1-(4-tert-butylphenyl)-3-phenoxyprop-1-en-1-yl]-3-chloro-2-methoxypyridine as a yellow oil (212 mg, 87%).

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated from the reaction solution under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-696dd793e7c5416aab80ddcb33fad528
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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