Bis(trimethylsilyl)carbodiimide → HCID 178511866, compound

HRID 2096555Notes

Reaction equation

HRID 2096555 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]3[C:19](=[CH:20][CH:21]=2)[O:18][C:12]2([CH2:17][CH2:16][CH2:15][O:14][CH2:13]2)[CH2:11][C:10]3=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([N:27]=[C:28]=[N:29][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:19](=[CH:20][CH:21]=2)[O:18][C:12]2([CH2:17][CH2:16][CH2:15][O:14][CH2:13]2)[CH2:11]/[C:10]/3=[N:29]\[C:28]#[N:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584237696-Cyclohexyl-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one

Product 1

HCID 178511866HCID 178511866, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-cyclohexyl-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (240 mg, 0.804 mmol) in anhydrous DCM (10 mL) was added TiCl4 (1 M solution in DCM, 608.6 mg, 3.2 mmol) dropwise within 15 min at room temperature. The mixture was stirred for 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (380.6 mg, 3.12 mmol) dropwise. The resulting mixture was stirred for another 18 h after the addition. The reaction mixture was poured into ice-water (100 g) and extracted with DCM (3×50 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give (E)-N-(6-cyclohexyl-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-ylidene)cyanamide (20 mg, 10%), which was used for next step without further purification.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred for another 18 h
  3. additionafter the addition
  4. extractionextracted with DCM (3×50 mL)
  5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-075d6e1d38354e29bebd58591fe363c4
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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