Diethyl Ether → HCID 57485781, compound
Reaction equation
[O:1]1[C:5]2([CH2:10][CH:9]([C:11](OC)=[O:12])[CH2:8][CH:7]([C:15](OC)=[O:16])[CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[OH-].[Na+]>C1COCC1>[OH:16][CH2:15][CH:7]1[CH2:8][CH:9]([CH2:11][OH:12])[CH2:10][C:5]2([O:1][CH2:2][CH2:3][O:4]2)[CH2:6]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of dimethyl 1,4-dioxaspiro[4.5]decane-7,9-dicarboxylate (6.0 g, 23 mmol) in dry THF at 0° C. was added lithium aluminum hydride (4.67 g, 68.7 mmol) under argon. The reaction was then refluxed overnight. The reaction was cooled to 0° C., and diethyl ether (100 ml) was added followed by drop-wise addition of 5 N NaOH until the gray lithium aluminum hydride was converted to a white solid. The reaction mixture was then filtered through a Celite pad, which was then washed with diethyl ether (100 ml). The combined filtrates were dried over sodium sulfate, filtered and concentrated by rotary evaporation to give the alcohol as a viscous colorless liquid (6.3 g, 93%).
Workup
- temperatureThe reaction was then refluxed overnight
- filtrationThe reaction mixture was then filtered through a Celite pad, which
- washwas then washed with diethyl ether (100 ml)
- dry with materialThe combined filtrates were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-213367464c1b4d9ab568cb39850bb251
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897611B2
Reaction notes
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