Diisobutylaluminumhydride → 3-(((1,1-Dimethylethyl)dimethylsilyl)oxy)cyclobutanol

HRID 473372Notes

Reaction equation

HRID 473372 reaction equation
C([O:7][CH:8]1[CH2:11][CH:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9]1)(=O)C(C)(C)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Si:13]([O:12][CH:10]1[CH2:11][CH:8]([OH:7])[CH2:9]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 575158723-(tert-Butyldimethylsilyloxy)cyclobutyl pivalate

Product 1

HCID 575158733-(((1,1-Dimethylethyl)dimethylsilyl)oxy)cyclobutanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(tert-butyldimethylsilyloxy)cyclobutyl pivalate (4.32 g, 15 mmol) in THF (20 ml) at 0° C. was added diisobutylaluminum hydride, 1.0 m solution in hexanes (48 ml, 48 mmol) dropwise. The reaction was stirred in 1 h, then slowly quenched with Rochelle's salt. The quenched mixture was stirred and layers were separated. The organic layer was dried over MgSO4 and concentrated to give the title compound as a colorless oil.

Workup

  1. customslowly quenched with Rochelle's salt
  2. stirringThe quenched mixture was stirred
  3. customlayers were separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd58414153264e8e8a36bde930214d08
Source dataset
uspto-grants-2014_01
Patent number
US08633315B2

Reaction notes

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