Diisobutylaluminumhydride → HCID 86606481, compound

HRID 2055196Notes

Reaction equation

HRID 2055196 reaction equation
[CH3:1][C@@H:2]1[CH2:7][C@H:6]([CH3:8])[CH2:5][C:4]([C:12]([O-:14])=[O:13])([C:9]([O-:11])=O)[CH2:3]1.[H-].[CH2:16]([Al+]CC(C)C)C(C)C>C(OCC)C>[CH3:16][O:14][C:12]([C:4]1([CH:9]=[O:11])[CH2:5][C@H:6]([CH3:8])[CH2:7][C@H:2]([CH3:1])[CH2:3]1)=[O:13]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86606482HCID 86606482, compound

Product 1

HCID 86606481HCID 86606481, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3R,5S)-3,5-dimethyl-cyclohexane-1,1-dicarboxylate (7.38 g, 32.4 mmol) in diethyl ether (250 mL) at −78° C. under a nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 43 mL, 64.8 mmol) dropwise. After 2.5 h, the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL) then with 1N HCl solution (100 mL). The aqueous phase was extracted with diethyl ether (100 mL×5), was dried (MgSO4) and was evaporated in vacuo to yield the title compound as a clear, colorless oil (5.5 g, 85%) which was used without further purification. MH+199.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL)
  2. extractionThe aqueous phase was extracted with diethyl ether (100 mL×5)
  3. dry with materialwas dried (MgSO4)
  4. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-07454dcbd1cd4e4a8d0ce8b3787815b3
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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