Aluminium lithium hydride → 3-(Undec-4z-enyloxy)benzyl alcohol

HRID 2091471Notes

Reaction equation

HRID 2091471 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22](OC)=[O:23])[CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CCOCC.O>[CH2:7]([O:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[CH2:22][OH:23])[CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57939201HCID 57939201, compound

Product 1

HCID 579392363-(Undec-4z-enyloxy)benzyl alcoholYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

35 mg of lithium aluminum hydride (922 μmol) are added, at 0° C., to 140 mg of 15 (460 μmol) in ether (3 mL). After reaction for 1 hour 30 minutes, the reaction medium is diluted with ether and hydrolyzed with two drops of water. After filtering through Celite, drying over Na2SO4 and concentrating, 127 mg of a colorless oil are isolated, i.e. a yield of 99%.

Workup

  1. customAfter reaction for 1 hour 30 minutes
  2. filtrationAfter filtering through Celite
  3. dry with materialdrying over Na2SO4
  4. concentrationconcentrating

Sources & evidence

ORD record
ord-3e65300dc3f34e6e8c7a1c12075464ea
Source dataset
uspto-grants-2013_05
Patent number
US08440591B2

Reaction notes

Loading…