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

HRID 1697220Notes

Reaction equation

HRID 1697220 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-3883320fbe6d4714a6f0c4cd6e87a1ba
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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