Pyridine → HCID 57707106, compound

HRID 1662581Notes

Reaction equation

C(Cl)Cl.[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([C:18](=O)[CH3:19])[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:21][C:22]1([CH3:30])[O:27][C:26](=[O:28])[CH2:25][C:24](=[O:29])[O:23]1.N1C=CC=CC=1>C1COCC1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:21][C:22]1([CH3:30])[O:27][C:26](=[O:28])[C:25](=[C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:13]=2)[CH3:19])[C:24](=[O:29])[O:23]1

Participants

Conditions

Temperature: 0 °C

Procedure

A 1.0M solution of titanium tetrachloride in DCM (9.3 mL, 9.3 mmol) was injected dropwise to THF (15 mL) cooled to 0° C. A solution of 1-(3-(benzyloxy)phenyl)ethanone (1.0 g, 4.42 mmol) (commercially available from Aldrich) and 2,2-dimethyl-1,3-dioxane-4,6-dione (701 mg, 4.86 mmol) (commercially available from Aldrich) in THF (5 mL) was then injected dropwise into the flask followed by dropwise addition of pyridine (1.8 mL, 22.1 mmol). The reaction temperature was allowed to warm to room temperature and the mixture was stirred overnight. The reaction was then quenched with water, extracted with EtOAc, dried over MgSO4, and filtered. The solvent was removed and the resulting crude mixture was purified by silica gel flash chromatography (hexane:EtOAc=4:1 to 1:1) to afford 5-(1-(3-(benzyloxy)phenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 103.B (855 mg, 55% yield).

Workup

temperatureto warm to room temperature
customThe reaction was then quenched with water
extractionextracted with EtOAc
dry with materialdried over MgSO4
filtrationfiltered
customThe solvent was removed
customthe resulting crude mixture was purified by silica gel flash chromatography (hexane:EtOAc=4:1 to 1:1)

Sources & evidence

ORD record: ord-286efeae960c4d3ca470f26e099dfa34
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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