4-Methylmorpholine → (4-(Pyridin-4-yl)phenyl)methanol

HRID 395704Notes

Reaction equation

HRID 395704 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O-])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Na+].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 23673507Sodium 4-(pyridin-4-yl)benzoate

Product 1

HCID 2795556(4-(Pyridin-4-yl)phenyl)methanolYield 33.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium 4-(4-pyridyl)benzoate (500 mg, 2.26 mmol), and N-methylmorpholine (0.250 mL, 2.26 mmol) in tetrahydrofuran (12 mL) was treated with ethyl chloroformate (0.216 mL, 2.26 mmol). After 0.25 h, the mixture was treated with sodium borohydride (256 mg, 6.79 mmol) followed by methanol (24 mL) dropwise. After 0.5 h, the mixture was treated with 10% aqueous acetic acid and concentrated in vacuo. The residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide. The aqueous layer was extracted twice with ethyl acetate and the combined extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo to yield 140 mg of the title compound which was used without further purification.

Workup

  1. waitAfter 0.5 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialthe combined extracts were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60694848b49f48048039bf82c36c71d1
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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