Ethanol → HCID 73444833, compound

HRID 2187310Notes

Reaction equation

HRID 2187310 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.[CH:17]1([CH:22]=[CH:23][CH:24]([CH3:31])[CH2:25][C:26](OCC)=[O:27])[CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)C>Cl>[CH:17]1([CH:22]=[CH:23][CH:24]([CH3:31])[CH2:25][CH:26]=[O:27])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8058HexaneHCID 21225700DiisobutylaluminumhydrideHCID 69824954HCID 69824954, compound

Product 1

HCID 73444833HCID 73444833, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Diisobutylaluminum hydride (95 ml of 1.0 M solution in hexane) was added into a hexane (200 ml) solution of ethyl 5-cyclopentyl-3-methylpent-4-enoate (used in example 1; 20.0 g; 95 mmol), at −65° C. After 3 hours stirring at the same temperature, ethanol (3 ml) was added, and the reaction mixture was poured into an ice-cold NH4Cl solution (200 ml) and diluted with 2 N HCl (100 ml). The organic layer was separated, washed with brine (3×200 ml), dried (MgSO4), concentrated in vacuo, and purified by flash chromatography (hexane/MTBE 15:1) to give 10.9 g (69% yield) of 5-cyclopentyl-3-methylpent-4-enal.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with brine (3×200 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (hexane/MTBE 15:1)

Sources & evidence

ORD record
ord-b678cd07cc404cbea423af95f66b014d
Source dataset
uspto-grants-2002_06
Patent number
US06410000B1

Reaction notes

Loading…