Dichloromethane → HCID 54537938, compound

HRID 2392972Notes

Reaction equation

HRID 2392972 reaction equation
C(Cl)Cl.[O:4]=[P:5](Cl)(Cl)Cl.[C:9]([CH2:13][CH2:14][CH2:15][O:16][C:17](=[C:25]1[CH:32]2[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:34][CH:26]1[CH2:27]3)[CH2:31]2)[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1)([O:11][CH3:12])=[O:10].[C:35]([CH:37](O)[CH3:38])#[N:36]>ClCl.N1C=CC=CC=1.N1C=CC=CC=1>[C:9]([CH2:13][CH2:14][CH2:15][O:16][C:17](=[C:25]1[CH:26]2[CH2:34][CH:30]3[CH2:29][CH:28]([CH2:33][CH:32]1[CH2:31]3)[CH2:27]2)[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][P:5]([CH2:38][CH2:37][C:35]#[N:36])([CH2:38][CH2:37][C:35]#[N:36])=[O:4])[CH:19]=1)([O:11][CH3:12])=[O:10]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6572LactonitrileHCID 24813Phosphorus oxychlorideHCID 53824756HCID 53824756, compound

Product 1

HCID 54537938HCID 54537938, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 15387381Chloranyl--pyridine (1/1)Solvent

Procedure

A flask containing 5 mL of CH2Cl2 under a layer of argon was cooled in an ice bath. Pyridine (0.5 mL) was added followed by slow addition of POCl3 (465 mg) and stirring continued for 15 min. A solution of the alkene (360 mg) from step (g) in 0.5 mL of 1:1 CH2 Cl2 /pyridine was added dropwise. The ice bath was removed and the solution stirred for 135 min. To this solution was added 1.0 mL of pyridine and 0.69 mL of 2-cyanoethanol. The reaction mixture was stirred for 4 hours resulting in formation of a white precipitate. TLC showed formation of two materials. Adding an additional 200 μL of cyanoethanol caused the precipitate to dissolve but stirring over night was without effect. The solution was evaporated to dryness and the crude product purified chromatographically. 1H NMR (CDCl3) δ1.79-1.98 (m, 14H), 2.41 (t,2H), 2.61 (br s,1H), 2.80 (m,4H), 3.23 (br s,1H), 3.41 (t,2H), 3.65 (s,3H), 4.32-4.48 (m,4H), 7.15-7.37 (m,4H). ##STR28##

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe ice bath was removed
  3. stirringthe solution stirred for 135 min
  4. additionTo this solution was added 1.0 mL of pyridine and 0.69 mL of 2-cyanoethanol
  5. stirringThe reaction mixture was stirred for 4 hours
  6. customresulting in formation of a white precipitate
  7. dissolutionto dissolve
  8. stirringstirring over night
  9. customThe solution was evaporated to dryness
  10. customthe crude product purified chromatographically

Sources & evidence

ORD record
ord-33a1714413554829be4222b30b904aa0
Source dataset
uspto-grants-1998_09
Patent number
US05804103

Reaction notes

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