4-Isopropylphenol → 2-Chloro-3-{[4-(1-methylethyl)phenoxy]methyl}pyridine

HRID 1747908Notes

Reaction equation

HRID 1747908 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)([CH3:22])[CH3:21].[Cl:30][C:31]1[C:36]([CH2:37]O)=[CH:35][CH:34]=[CH:33][N:32]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:30][C:31]1[C:36]([CH2:37][O:29][C:26]2[CH:27]=[CH:28][C:23]([CH:20]([CH3:22])[CH3:21])=[CH:24][CH:25]=2)=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

6

Reactant 4

HCID 74654-IsopropylphenolHCID 11776TriphenylphosphineHCID 2763647(2-Chloropyridin-3-yl)methanolHCID 5462977Diethyl azodicarboxylate2×

Product 1

HCID 624715482-Chloro-3-{[4-(1-methylethyl)phenoxy]methyl}pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of triphenylphosphine (2740 mg), 4-isopropylphenol (1138 mg), (2-chloropyridin-3-yl)methanol (1000 mg) and dehydrated THF (20 mL) was added DEAD (40% toluene solution, 4549 mg) at room temperature over 30 min. The reaction mixture was stirred at room temperature for 2 hr, DEAD (40% toluene solution, 919 mg) was added at room temperature, and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1623 mg) as an orange oil.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-faaea308db1c4863945314fc52b8e3bc
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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