Hydrochloric Acid → HCID 66699541, compound

HRID 1161131Notes

Reaction equation

HRID 1161131 reaction equation
C([Mg]Cl)(C)C.I[C:7]1[CH:35]=[CH:34][C:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][Si](C)(C)C)=[CH2:20])=[C:15]([O:26][Si](C)(C)C)[C:14]=2[CH2:31][CH2:32][CH3:33])=[CH:9][CH:8]=1.[CH:36]([C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][N:45]=1)[C:41]#[N:42])=[O:37].Cl>O1CCCC1.O>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:10]2[CH:34]=[CH:35][C:7]([CH:36]([OH:37])[C:38]3[CH:39]=[C:40]([CH:43]=[CH:44][N:45]=3)[C:41]#[N:42])=[CH:8][CH:9]=2)=[C:14]([CH2:31][CH2:32][CH3:33])[C:15]=1[OH:26])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 147614682-FormylisonicotinonitrileHCID 66699606HCID 66699606, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 66699541HCID 66699541, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Add isopropyl magnesium chloride (2M solution in tetrahydrofuran, 2.98 mL, 5.95 mmol) to a solution of 1-(4-iodo-benzyloxy)-2-propyl-3-trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-benzene (3.00 g, 5.41 mmol) in tetrahydrofuran (0.1M) cooled to 0° C. After 15 minutes, warm reaction to room temperature. After 1 hour, cool the reaction to −78° C. Add a solution of 2-formyl-isonicotinonitrile (612 mg, 5.95 mmol) in tetrahydrofuran (10 mL) via syringe. After 1 hour, warm the reaction to room temperature. Add 10% hydrochloric acid (30 mL). After 5 minutes, pour the reaction into water and extract with ethyl acetate. Combine organics, dry with sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with methanol:dichloromethane followed by trituration with acetonitrile to yield the title product as a white solid (1.71 g, 76%): 1H NMR (CDCl3) δ 0.95 (t, 3H), 1.56 (sextet, 2H), 2.56 (s, 3H), 2.69 (t, 2H), 4.50 (d, 1H), 5.16 (s, 2H), 5.84 (d, 1H), 6.46 (d, 1H), 7.41 (m, 4H), 7.51 (s, 1H), 7.55 (d, 1H), 8.76 (d, 1H), 12.74 (s, 1H).

Workup

  1. temperaturewarm
  2. customreaction to room temperature
  3. waitAfter 1 hour
  4. temperaturecool
  5. customthe reaction to −78° C
  6. waitAfter 1 hour
  7. temperaturewarm
  8. customthe reaction to room temperature
  9. waitAfter 5 minutes
  10. additionpour
  11. extractionextract with ethyl acetate
  12. dry with materialCombine organics, dry with sodium sulfate
  13. filtrationfilter
  14. concentrationconcentrate under reduced pressure
  15. customto give a residue
  16. customPurify the residue by flash chromatography
  17. washeluting with methanol

Sources & evidence

ORD record
ord-a3123f03da3a449886ecd279065cccde
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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