Aluminium lithium hydride → HCID 57672481, compound

HRID 2101767Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])[C:8]([CH:11]2[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:11]1([C:8]2[C:7]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[F:22])=[CH:6][C:5]([CH2:3][OH:2])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a dry round bottom flask containing 13.3 (0.4 g, 1.328 mmol) under an argon atmosphere was added dry THF (6 mL). The resulting mixture was cooled to 0° C. After 15 minutes, lithium aluminum hydride (1.0 M solution in THF) (2.0 mL, 2.00 mmol) was carefully added at 0° C. Upon complete addition, the reaction was allowed to warm to room temperature. After 2 hours, the reaction was cooled in an ice bath, and then carefully quenched with water and diluted with EtOAc. The organic phase was washed with 2M HCl and then with brine. After drying over anhydrous magnesium sulfate, the organic solvent was removed under reduced pressure, and the residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 40% EtOAc in hexanes) to yield a colorless oil 13.4 (0.24 g, 66% yield.).

Workup

additionUpon complete addition
temperatureto warm to room temperature
waitAfter 2 hours
temperaturethe reaction was cooled in an ice bath
customcarefully quenched with water
additiondiluted with EtOAc
washThe organic phase was washed with 2M HCl
dry with materialAfter drying over anhydrous magnesium sulfate
customthe organic solvent was removed under reduced pressure
customthe residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-008b07fe608d42bca3453b4dc5f6a9d7
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572934B2

Reaction notes

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