Acetaldehyde → (S,E)-4-(3,4-dichlorophenyl)-2-ethylidene-3,4-dihydronaphthalen-1(2H)-one

HRID 556159Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:30](=O)[CH3:31]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])/[C:11](=[CH:30]/[CH3:31])/[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1 (2H)-one 1 (3.0 g, 10.3 mmol) in THF (50 mL) at −78 ° C was added LiHMDS (1.0 M, 12.4 mL, 12.4 mmol). The reaction mixture was stirred for 20 min before acetaldehyde (0.55 g, 0.70 mL, 12.41 mmol) was added. The reaction mixture was stirred and warmed to 0° C. over 2 h before being quenched with a saturated solution of NH4Cl (10 mL). The product was extracted with ethyl acetate, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:7 to 1:5) to give (S,E)-4-(3,4-dichlorophenyl)-2-ethylidene-3,4-dihydronaphthalen-1(2H)-one 42 (2.9 g, 88%).

Workup

additionwas added
custombefore being quenched with a saturated solution of NH4Cl (10 mL)
extractionThe product was extracted with ethyl acetate
customdried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:7 to 1:5)

Sources & evidence

ORD record: ord-95a7ec9a810946a4ac46847c4b8dcb52
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053603B2

Reaction notes

Loading…