Water → (2S)-2-(3,4-dichlorophenyl)pent-4-en-1-ol

HRID 1737443Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH:14]=[CH2:15])[C:10](O)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH:14]=[CH2:15])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-(S)-(3,4-dichlorophenyl)-4-pentenoic acid (7.0 gm) (prepared as described by J. Hale et. al., Bioorganic & Medicinal Chemistry Letters 1993,3, 319-322.) in ether (50 mL) at r.t. was added portionwise over 5 min solid lithium aluminum hydride (700 mg). The reaction was heated to 40° C. for 3 hr and then stirred at r.t. for 16 hr. The reaction was poured into water containing 25 mL of 2N NaOH and extracted twice with ether. The ether layers were washed with brine, combined and dried over Na2SO4. Flash chromatograghy afforded the title compound (4.5 gm) as an oil. [α]D =+14 (EtOH, c=1.5).

Workup

extractionextracted twice with ether
washThe ether layers were washed with brine
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-64184318dda740a8973b20ed3d35f2e3
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05962462

Reaction notes

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