Thionyl Chloride → HCID 18448592, compound

HRID 32050Notes

Reaction equation

HRID 32050 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7](O)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1)#[N:2].O=S(Cl)[Cl:16]>C(Cl)Cl>[Cl:16][CH:7]1[C:6]2[C:11](=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 184486127-Cyano-4-chromanol

Product 1

HCID 18448592HCID 18448592, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

7-Cyano-4-chromanol (Step B) (8.0 g, 46 mmol) was dissolved in CH2Cl2 (120 mL) and cooled to 10° C. SOCl2 (5.0 mL, 70 mmol) was added, the reaction was warmed to RT and stirred overnight. The reaction was concentrated in vacuo and azeotroped with CH2Cl2 (2×50 mL). The residue was dissolved in EtOAc (500 mL), washed with saturated NaHCO3 (250 mL), and with brine (150 mL), dried over MgSO4, filtered and concentrated in vacuo to provide the title compound which was used without further purification.

Workup

  1. temperaturethe reaction was warmed to RT
  2. concentrationThe reaction was concentrated in vacuo
  3. customazeotroped with CH2Cl2 (2×50 mL)
  4. dissolutionThe residue was dissolved in EtOAc (500 mL)
  5. washwashed with saturated NaHCO3 (250 mL)
  6. dry with materialwith brine (150 mL), dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24b5b25dfecc4510886968d66f9bcdce
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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