Aluminium lithium hydride → 3,3-Bis(4-fluorophenyl)propanol

HRID 2190301Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 3,3-bis(4-fluorophenyl)propanoate, prepared in the previous step, in THF (75 mL) at −78° C. was added LAH (1 M in PhMe, 35 mL, 35.0 mmol). The reaction mixture was warmed to 0° C. over 15 min, quenched with 6 mL of water, 12 mL of 2.5 M NaOH, followed by 18 mL of water. The mixture was stirred at room temperature for 30 min. The solids were removed by filtration and the solution was concentrated to provide 3,3-bis(4-fluorophenyl)propan-1-ol which was used in the next step without further purification.

Workup

customquenched with 6 mL of water, 12 mL of 2.5 M NaOH
customThe solids were removed by filtration
concentrationthe solution was concentrated

Sources & evidence

ORD record: ord-f9b4b2e809d24878958f75cea20b2047
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324396B2

Reaction notes

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