Lithium borohydride → 5-Benzyloxy-1,3-pentanediol

HRID 1586905Notes

Reaction equation

HRID 1586905 reaction equation
[OH:1][C@@H:2]([CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4](OC)=[O:5].[BH4-].[Li+]>C1COCC1.O>[CH2:11]([O:10][CH2:9][CH2:8][CH:2]([OH:1])[CH2:3][CH2:4][OH:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 10879179HCID 10879179, compound

Product 1

HCID 197601555-Benzyloxy-1,3-pentanediol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(S)-hydroxy-5-benzyloxypentanoate (38, Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R., J. Am. Chem. Soc. 1988, 110 629-631) (183 mmol) in anhydrous THF (1 l) is added lithium borohydride (7.7 g, excess) at 0° C. over 15 min. The reaction mixture is stirred at RT for 30 minutes, and then refluxed for 6 hours. The mixture is then cooled to 0° C., diluted with water (60 ml), and stirred overnight at RT. A white precipitate is removed by filtration, the solvent removed in vacuum, and the residue distilled under vacuum to yield 5-benzyloxy-1,3-pentanediol 39.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureThe mixture is then cooled to 0° C.
  3. stirringstirred overnight at RT
  4. customA white precipitate is removed by filtration
  5. customthe solvent removed in vacuum
  6. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-31109c18c3bb4b3283a7183826bd7b1b
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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