Water → HCID 69825517, compound

HRID 2185147Notes

Reaction equation

HRID 2185147 reaction equation
[CH:1]1([CH:6]=[CH:7][CH:8]([CH3:15])[CH2:9][C:10](OCC)=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH:1]1([CH:6]=[CH:7][CH:8]([CH3:15])[CH2:9][CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69824954HCID 69824954, compound

Product 1

HCID 69825517HCID 69825517, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of ethyl 5-cyclopentyl-3-methylpent-4-enoate (16.8 g; 80 mmol; obtained according to Streinz, L., Romanuk, M., Sorm, F., Sehnal, F. DE 2 444 837, priority 20.09.1973) in diethyl ether (30 ml) was added dropwise to a suspension of lithium aluminum hydride (3.0 g; 80 mmol) in the same solvent (110 ml), and the reaction mixture was stirred at reflux for 1 hour. Water (3.5 ml), then 15% NaOH solution, and again water (3.5 ml) were added, the precipitate filtered off and washed with MTBE (30 ml). The combined organic phases were washed with 1 N HCl (200 ml) and brine (3×100 ml), dried (MgSO4), concentrated in vacuo, and distilled (79-82° C./0.07 torr) to give 7.8 g (59% yield) of 5-cyclopentyl-3-methylpent-4-en-1-ol.

Workup

  1. customobtained
  2. temperatureat reflux for 1 hour
  3. filtrationthe precipitate filtered off
  4. washwashed with MTBE (30 ml)
  5. washThe combined organic phases were washed with 1 N HCl (200 ml) and brine (3×100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. distillationdistilled (79-82° C./0.07 torr)

Sources & evidence

ORD record
ord-87175c4b74374d2baf691a3132d9ae18
Source dataset
uspto-grants-2002_06
Patent number
US06399811B1

Reaction notes

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