Bis(trimethylsilyl)carbodiimide → HCID 178511868, compound

HRID 2096545Notes

Reaction equation

HRID 2096545 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[O:12][C:7]1([CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6][C:5]2=O.[C:17](=[N:23][Si](C)(C)C)=[N:18][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[O:12][C:7]1([CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6]/[C:5]/2=[N:23]\[C:17]#[N:18]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58424598HCID 58424598, compound

Product 1

HCID 178511868HCID 178511868, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-4′,5′-dihydro-2′H-spiro[chroman-2,3′-furan]-4-one (206 mg, 0.731 mmol) in anhydrous DCM (6 mL) was added TiCl4(281 mg, 1.48 mmol) dropwise within 15 minutes at room temperature and resulting mixture was stirred for 1 h. To this mixture was added N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (300 mg, 1.61 mmol). The resulting mixture was stirred for another 18 hours after addition. The reaction mixture was poured into water-ice and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated to give crude product (225 mg, 100%), which was used in the next step without further purification.

Workup

  1. customresulting mixture
  2. stirringThe resulting mixture was stirred for another 18 hours
  3. additionafter addition
  4. extractionextracted with DCM
  5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e10146c9052c44b293b1fc7208fc354d
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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