Diisobutylaluminumhydride → HCID 131728086, compound

HRID 645454Notes

Reaction equation

HRID 645454 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1([CH3:32])[CH2:10][CH2:9][CH:8]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:12][SiH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:7]1([CH3:31])[CH3:30].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[C:14]([SiH2:13][O:12][C:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]1[CH2:9][CH2:10][C:6]([CH:5]=[CH:4][CH2:3][OH:2])([CH3:32])[C:7]1([CH3:31])[CH3:30])([CH3:15])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 131728084HCID 131728084, compound

Product 1

HCID 131728086HCID 131728086, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Intermediate (5) (11.12 g, 23.92 mmol) in CH2Cl2 (150 mL ) at −78° C. was added dropwise diisobutylaluminium hydride (1.5 M solution in toluene; 63.8 mL, 95.67 mmol) over a period of 30 minutes. After stirring at −78° C. for 2 hours, the reaction mixture was allowed to warm to −55° C. over a period of 2 hours and the reaction was quenched by the addition of a 2 N K-Na-tartrate solution (100 mL). H2O (400 mL) was added and the aqueous layer was extracted with Et2O (4×150 mL). The combined organic layers were dried over anhydrous MgSO4, the solvent removed in vacuo and the resulting residue was purified over silica (n-hexane/ethyl acetate, 85:15) to afford 10.34 g (99% yield) of the desired intermediate (6) as a colourless oil which was characterized as follows:

Workup

  1. temperatureto warm to −55° C. over a period of 2 hours
  2. customthe reaction was quenched by the addition of a 2 N K-Na-tartrate solution (100 mL)
  3. additionH2O (400 mL) was added
  4. extractionthe aqueous layer was extracted with Et2O (4×150 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customthe solvent removed in vacuo
  7. customthe resulting residue was purified over silica (n-hexane/ethyl acetate, 85:15)

Sources & evidence

ORD record
ord-23ee75e4498c479bbf7ff7d69f8f2b9b
Source dataset
uspto-grants-2010_04
Patent number
US07704986B2

Reaction notes

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