Tetrahydrofuran → (E)-3-{8-(4-fluoro-3-methylphenyl)-10,10-dimethyl-1,5dithiaspiro{5.5}undec-8-en-9-yl}propenal

HRID 359559Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.C(=NC1CCCCC1)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:26][C:27]3([CH2:33][C:34]([CH3:39])([CH3:38])[C:35]=2C=O)[S:32][CH2:31][CH2:30][CH2:29][S:28]3)=[CH:21][C:20]=1[CH3:40].[CH2:41]1C[O:44][CH2:43][CH2:42]1>CCOCC>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:26][C:27]3([CH2:33][C:34]([CH3:38])([CH3:39])[C:35]=2/[CH:41]=[CH:42]/[CH:43]=[O:44])[S:28][CH2:29][CH2:30][CH2:31][S:32]3)=[CH:21][C:20]=1[CH3:40]

Participants

Conditions

Temperature: -78 °C

Procedure

To a -20° C. solution of LDA (19.0 mmol) in 60 mL anhydrous THF was added ethylidenecyclohexylamine (Org. Syn. 50, 66) (2.38 gm, 19.0 mmol). The solution was stirred for 30 min, cooled to -78° C. and a solution of 8 (3.50 g, 10.0 mmol) in 60 mL was added. The mixture was stirred for 3 h, diluted with ether and quenched with H2O. The organic layer was washed with H2O and brine and dried (MgSO4). Removal of the volatiles in vacuo and purification of the residue by HPLC. using 10:1 hexanes:EtOAc provided 1.6 g of the orange color gum.

Workup

stirringThe mixture was stirred for 3 h
customquenched with H2O
washThe organic layer was washed with H2O and brine
dry with materialdried (MgSO4)
customRemoval of the volatiles
customin vacuo and purification of the residue by HPLC
customEtOAc provided 1.6 g of the orange color gum

Sources & evidence

ORD record: ord-69e39f5144c145e6b746ee31762868ae
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05001144

Reaction notes

Loading…