HCID 18314568, compound → HCID 18314557, compound

HRID 265800Notes

Reaction equation

HRID 265800 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

4

Reactant 1

HCID 18314568HCID 18314568, compound2×

Product 1

HCID 18314557HCID 18314557, compound

Reagents, catalysts & solvents 2

HCID 24813Phosphorus oxychlorideCatalystHCID 1049PyridineSolvent

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-trimethylsiloxynaphth-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 yield the title compound as a pale yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured
  3. custominto crushed ice
  4. extractionThe mixture was extracted with Et2O
  5. washthe combined organic layers were washed with water, dilute HCl and water
  6. concentrationThe organic phase was concentrated in vacuo to a gummy residue which
  7. customwas purified by flash chromatography (silica, 20% EtOAc-hexane)

Sources & evidence

ORD record
ord-5f24e720d79a4ce0aad3968f7366fa1b
Source dataset
uspto-grants-1997_07
Patent number
US05648514

Reaction notes

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