Borane → 3-Pyridinehexanol

HRID 1583419Notes

Reaction equation

HRID 1583419 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=[O:13])[CH:2]=1.B>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:2]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 129045606-(Pyridin-3-yl)hexanoic acid

Product 1

HCID 36861733-PyridinehexanolYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 26.6 g of 3-pyridinehexanoic acid in 200 ml of dry tetrahydrofuran was cooled in an ice bath as 488 ml of 1 molar borane in tetrahydrofuran was added slowly. The reaction mixture was gradually brought to reflux temperature and was heated overnight. The excess reagent was quenched by the careful addition of 100 ml of methanol and the mixture was concentrated. The residue was diluted with excess 6N hydrochloric acid, allowed to stand overnight, made basic with 50% sodium hydroxide, and extracted with dichloromethane. The combined organic layers were dried over potassium carbonate, and evaporated to an oil which was distilled to give 22.6 g (92%) of 6-(3-pyridyl)hexanol, bp 180°-200° C./0.2 mm.

Workup

  1. additionwas added slowly
  2. temperatureto reflux temperature
  3. temperaturewas heated overnight
  4. customThe excess reagent was quenched by the careful addition of 100 ml of methanol
  5. concentrationthe mixture was concentrated
  6. additionThe residue was diluted with excess 6N hydrochloric acid
  7. extractionextracted with dichloromethane
  8. dry with materialThe combined organic layers were dried over potassium carbonate
  9. customevaporated to an oil which
  10. distillationwas distilled

Sources & evidence

ORD record
ord-d02628c9675349e59934a48d96ffb0c2
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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