Diisobutylaluminum hydride → HCID 53924344, compound

HRID 981014Notes

Reaction equation

HRID 981014 reaction equation
[C:1]([CH:5]1[O:19][CH:18]2[CH:7]([CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]2)[O:6]1)([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:2][C:1]([CH3:4])([CH3:3])[CH2:5][O:6][CH:7]1[CH:18]([OH:19])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54008400HCID 54008400, compound

Product 1

HCID 53924344HCID 53924344, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Preparation steps identical to those described in example 1(b) were carried out using 5.2 g of 14-tert-butyl-13,15-dioxabicyclo[10.3.0]pentadeca-4,8-diene and 32.8 ml of a 1.2M solution of DIBAH in toluene. After acidification, the reaction mixture was washed with ether, then with brine, dried, concentrated and distilled in a bulb-to-bulb apparatus. 4.82 g of 12-(2,2-dimethylpropoxy)-4,8-cyclododecadien-1-ol were obtained.

Workup

  1. customPreparation steps identical to
  2. washAfter acidification, the reaction mixture was washed with ether
  3. dry with materialwith brine, dried
  4. concentrationconcentrated
  5. distillationdistilled in a bulb-to-bulb apparatus

Sources & evidence

ORD record
ord-aa154650a7714318b52ad0f9be4add43
Source dataset
uspto-grants-1991_02
Patent number
US04990495

Reaction notes

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