Tetrahydrofuran → (2-Bromopyridin-3-yl)methanol

HRID 2086588Notes

Reaction equation

HRID 2086588 reaction equation
ClC(OCC)=O.[Br:7][C:8]1[C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1.CCN(CC)CC.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1(C)C=CC=CC=1>[Br:7][C:8]1[C:13]([CH2:14][OH:15])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2332622-Bromopyridine-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 14761460(2-Bromopyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add ethyl chloroformate (3.17 g, 29.28 mmol) to a solution of 2-bromo-3-pyridinecarboxylic acid (5.63 g, 27.89 mmol) and Et3N (2.96 g, 29.28 mmol) in toluene (150 ml) at RT and stir for 1 h., filter and concentrate. Dissolve the residue in THF (93 ml), add to a suspension of LiAlH4 (1.11 g, 29.28 mmol) in THF (37 mmol) dropwise at −78° C. and stir for 30 min. Quench the reaction with saturated aqueous NH4Cl, stir at RT for 1 h, filter through celite, extract with EtOAc, dry over Na2SO4 and concentrate. Purify the residue by column chromatography to produce the desired compound.

Workup

  1. filtrationfilter
  2. concentrationconcentrate
  3. dissolutionDissolve the residue in THF (93 ml)
  4. stirringstir for 30 min
  5. customQuench
  6. customthe reaction with saturated aqueous NH4Cl
  7. stirringstir at RT for 1 h
  8. filtrationfilter through celite
  9. extractionextract with EtOAc
  10. dry with materialdry over Na2SO4
  11. concentrationconcentrate
  12. customPurify the residue by column chromatography

Sources & evidence

ORD record
ord-8ae341e94e3e4e16af7d6f90e58529f2
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

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