Bis(trimethylsilyl)carbodiimide → HCID 178422831, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8]1)[CH2:6][C:5]2=O.C[Si]([N:22]=[C:23]=[N:24][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8]1)[CH2:6]/[C:5]/2=[N:24]\[C:23]#[N:22]Participants
Procedure
To a solution of 6-bromo-3′-methylspiro[chroman-2,1′-cyclopentan]-4-one (216 mg, 0.73 mmol) in anhydrous DCM (5.7 mL) was added TiCl4 (1 M solution in DCM, 1.5 mL, 1.49 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 (300 mg, 0.36 mL, 1.61 mmol) dropwise. The resulting mixture was stirred for another 18 h after the addition. The reaction mixture was poured into ice-water (20 g) and extracted with DCM (3×20 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give (E)-N-(6-bromo-3′-methylspiro[chroman-2,1′-cyclopentane]-4-ylidene)cyanamide as light brown solid (225 mg), which was used in the next step without further purification.
Workup
- additionafter the addition
- stirringThe resulting mixture was stirred for another 18 h
- additionafter the addition
- extractionextracted with DCM (3×20 mL)
- dry with materialThe combined organic phases were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3539d2eb61af4dc8ac517aa0cdbe117b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921359B2
Reaction notes
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