Diisobutylaluminumhydride → 8-(tert-Butyldimethylsilyloxy)-2,2-dimethyloctan-1-ol
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:22])([CH3:21])[C:16](OCC)=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>CCOCC>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:22])([CH3:21])[CH2:16][OH:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 8-(tert-butyldimethylsilyloxy)-2,2-dimethyloctanoate (example 279, step a) (20 g) in dry ether under nitrogen (300 mL) was cooled to 0° C. in an ice bath then diisobutylaluminium hydride (1M in toluene, 133 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 1 hour then quenched with saturated aqueous potassium sodium tartrate (Rochelle's salt, 400 mL) and stirred overnight. The mixture was extracted with ethyl acetate (3×300 mL) then the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. Purification was by silica gel chromatography eluting with 0-20% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless liquid. Yield 10.11 g.
Workup
- customthen quenched with saturated aqueous potassium sodium tartrate (Rochelle's salt, 400 mL)
- stirringstirred overnight
- extractionThe mixture was extracted with ethyl acetate (3×300 mL)
- washthe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customPurification
- washeluting with 0-20% ethyl acetate in cyclohexane
Sources & evidence
- ORD record
- ord-e7d70e3d251744d29e866c5cd9d54917
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629271B2
Reaction notes
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