HCID 18314568, compound → HCID 18314557, compound

HRID 2393857Notes

Reaction equation

[C:1]([C:3]1(O[Si](C)(C)C)[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([C:15]#[C:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=3)[CH:6]=[CH:5][C:4]1=2)#[N:2]>P(Cl)(Cl)(Cl)=O.N1C=CC=CC=1>[C:1]([C:3]1[C:4]2[CH:5]=[CH:6][C:7]([C:15]#[C:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=3)=[CH:8][C:9]=2[C:10]([CH3:13])([CH3:14])[CH2:11][CH:12]=1)#[N:2]

Participants

Conditions

Temperature: 115 °C

Procedure

To 215 mg (0.48 mmol) of ethyl 4-[(5-cyano-5,6,7,8-tetrahydro-8,8-dimethyl-5-tri-methylsiloxynaphth-2-yl)ethynyl]benzoate (Compound 107) was added 0.5 ml of pyridine and 3 drops of phosphorous oxychloride. The resulting dark mixture was gently refluxed at 115° C. for 30 minutes, cooled to room temperature and poured into crushed ice. The mixture was extracted with Et2O and the combined organic layers were washed with water, dilute HCl and water. The organic phase was concentrated in vacuo to a gummy residue which was purified by flash chromatography (silica, 20% EtOAc-hexane) to as the title compound as a pale yellow solid.

Workup

temperaturecooled to room temperature
additionpoured
custominto crushed ice
extractionThe mixture was extracted with Et2O
washthe combined organic layers were washed with water, dilute HCl and water
concentrationThe organic phase was concentrated in vacuo to a gummy residue which
customwas purified by flash chromatography (silica, 20% EtOAc-hexane) to as the title compound as a pale yellow solid

Sources & evidence

ORD record: ord-51dc699be5134f93a846d30a0c9e9303
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808083

Reaction notes

Loading…