Tetrahydrofuran → 1-(4-(tert-Butyl)pyridin-2-yl)ethanol

HRID 1637731Notes

Reaction equation

HRID 1637731 reaction equation
C[Mg]Br.O1CCC[CH2:5]1.[C:9]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH:19]=[O:20])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>C(OCC)C>[C:9]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH:19]([OH:20])[CH3:5])[CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 187996954-(tert-butyl)picolinaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 187996571-(4-(tert-Butyl)pyridin-2-yl)ethanolYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methylmagnesium bromide (9.7 ml, 29 mmole) is added to 20 ml dry tetrahydrofuran in an oven dried 100 ml two neck round bottom flask under nitrogen at 0° C. The solution is treated with 4-t-Butyl-2-pyridine-carboxaldehyde (3.8 g, 23.3 mmole) in 2×5 ml diethyl ether followed by 10 ml diethyl ether. The reaction is warmed to room temperature and then to reflux for 1 h. The mixture is cooled to 0° C., is quenched with 1×20 ml 10% hydrochloric acid, and the pH is adjusted to 9 with 2 N sodium hydroxide. The layers are separated, the aqueous layer is extracted with 4×25 ml dichloromethane, and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to give 3.9 g (93%) of 4-t-Butyl-2-(1-hydroxyethyl)-pyridine as a tan solid. Analytical material is obtained via recrystallization from hexane.

Workup

  1. dry with materialdried 100 ml two neck round bottom flask under nitrogen at 0° C
  2. temperatureto reflux for 1 h
  3. temperatureThe mixture is cooled to 0° C.
  4. customis quenched with 1×20 ml 10% hydrochloric acid
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with 4×25 ml dichloromethane
  7. dry with materialthe combined organics are dried over potassium carbonate
  8. concentrationThe dried organics are concentrated in vacuo

Sources & evidence

ORD record
ord-1798a77924cc4307a9b58174e8ada42e
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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