HCID 18314568, compound → HCID 18314557, compound

HRID 610338Notes

Reaction equation

HRID 610338 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-1105d5412b2f4da7b79cfa49bc882da7
Source dataset
uspto-grants-1999_12
Patent number
US05998471

Reaction notes

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