hexahydro-cyclopenta[b]furan-2-one → 3-Octanol

HRID 2293597Notes

Reaction equation

HRID 2293597 reaction equation
[CH:1]12[CH2:8][CH2:7]C[CH:5]1[CH2:4]C(=O)[O:2]2.[H-].C([Al+]C[CH:17]([CH3:19])[CH3:18])C(C)C>C1(C)C=CC=CC=1>[CH3:4][CH2:5][CH:1]([OH:2])[CH2:8][CH2:7][CH2:19][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 11665410hexahydro-cyclopenta[b]furan-2-oneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 115273-Octanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound (52) (12.1 g) was reduced with diisobutylaluminum hydride (1.5M, 65.1 ml) in toluene (500 ml) at -78° C. and the obtained crude product was subjected to silicagel column chromatography to give the titled compound (53). Yield: 11.1 g (91%).

Workup

  1. customthe obtained crude product

Sources & evidence

ORD record
ord-f3d81bbb58614820bada496856e44850
Source dataset
uspto-grants-1997_11
Patent number
US05686487

Reaction notes

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