Bis(trimethylsilyl)carbodiimide → HCID 58424515, compound

HRID 2096641Notes

Reaction equation

HRID 2096641 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:7]=[C:8]3[C:18](=[CH:19][CH:20]=2)[O:17][C:11]2([CH2:16][CH2:15][CH2:14][O:13][CH2:12]2)[CH2:10][C:9]3=O)[CH2:3][CH2:2]1.C[Si]([N:26]=[C:27]=[N:28][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH:1]1([C:4]#[C:5][C:6]2[CH:7]=[C:8]3[C:18](=[CH:19][CH:20]=2)[O:17][C:11]2([CH2:16][CH2:15][CH2:14][O:13][CH2:12]2)[CH2:10][C:9]3=[N:28][C:27]#[N:26])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58424292HCID 58424292, compound

Product 1

HCID 58424515HCID 58424515, compoundYield 128.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(cyclopropylethynyl)-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (76 mg, 0.27 mmol) in anhydrous DCM (15 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 0.54 mL, 0.54 mmol) dropwise within 15 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (0.16 mL, 0.427 mmol) dropwise. The resulting mixture was stirred 80 h. The reaction mixture was quenched with ice-water (15 g), and stirred for 30 min, then it was transferred to a separating funnel, the separated aqueous phase was extracted 2 times with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give 106 mg the crude desired product as light yellow solid, which was used for next step without further purification. MS ESI +ve m/z 307 (M+H)+.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred 80 h
  3. customThe reaction mixture was quenched with ice-water (15 g)
  4. stirringstirred for 30 min
  5. customit was transferred to a separating funnel
  6. extractionthe separated aqueous phase was extracted 2 times with DCM
  7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c6145c3e4e79476b9d97c05ab89a0c99
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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