Hydrochloric Acid → HCID 11173271, compound
Reaction equation
[Li+].[CH3:2][Si]([N-][Si](C)(C)C)(C)C.C1(C2C=CC=C[C:18]=2[OH:23])C=CC=CC=1.[C:24]1([C:30]#[C:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.[C:39]1(C)C=C[CH:42]=[CH:41][CH:40]=1>>[C:32]1([C:31]#[C:30][C:24]2[CH2:2][O:23][CH2:18][C:29]=2[C:28]#[C:27][C:26]2[CH:25]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1Participants
Procedure
1.04 g (0.63 mmol) of the diyne complex was dissolved in 5 mL of THF and added by pipette dropwise to LiHMDS (210 mg, 1.26 mmol) dissolved in 20 mL of THF. After 45 minutes, the reaction mixture was concentrated to a dark brown oil. Pentane was added and the mixture was filtered through Celite. The filtrate was transferred to a 100 mL round bottom flask, concentrated and dissolved in 10 mL of toluene. 640 mg (3.76 mmol) of 2-phenylphenol dissolved in 5 mL of toluene was added, the color of the solution changes from green-brown to deep red. After 1 h, 670 mg (3.76 mmol) of diphenylacetylene was added. After 1 h, 1M HCl was added and after typical work-up and column chromatography, 51 mg (30%) of the enediyne was isolated as a pale yellow solid, see spectral data above.
Workup
- concentrationthe reaction mixture was concentrated to a dark brown oil
- additionPentane was added
- filtrationthe mixture was filtered through Celite
- customThe filtrate was transferred to a 100 mL round bottom flask
- concentrationconcentrated
- dissolutiondissolved in 10 mL of toluene
- additionwas added
- waitAfter 1 h
- waitAfter 1 h
- customafter typical work-up and column chromatography, 51 mg (30%) of the enediyne was isolated as a pale yellow solid
Sources & evidence
- ORD record
- ord-1042cfbd980e4bc1826105402283096d
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06967256B2
Reaction notes
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