Aluminium lithium hydride → HCID 23018031, compound

HRID 1788379Notes

Reaction equation

C([O:3][C:4](=O)[C:5](=[C:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[CH3:6])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[O:10]1[CH2:11][CH2:12][C:7](=[C:5]([CH3:6])[CH2:4][OH:3])[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 4.2 g (24.39 mmol) of 2-(tetrahydropyran-4-ylidene)propionic acid ethyl ester obtained in the above 1) in ether (50 mL) was added 1.20 g (31.7 mmol) of lithium aluminum hydride under an atmosphere of argon, and stirred for 1 hour at 0° C., followed by stirring for 2 hours at room temperature. After the reaction mixture was diluted with ether, excess reagent was carefully quenched with ethanol and aqueous ammonium chloride solution. After drying of the reaction mixture with anhydrous magnesium sulfate and subsequent evaporation of the solvent, 4.2 g (yield 100%) of 2-(tetrahydropyran-4-ylidene)propan-1-ol was obtained as colorless liquid. Its physical property is shown below.

Workup

stirringby stirring for 2 hours at room temperature
customwas carefully quenched with ethanol and aqueous ammonium chloride solution
dry with materialAfter drying of the reaction mixture with anhydrous magnesium sulfate and subsequent evaporation of the solvent

Sources & evidence

ORD record: ord-1188d8bcd25241758846be29e41c10d6
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511144B2

Reaction notes

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