Chlorotrimethylsilane → HCID 10535797, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:12](O)[CH:13]=[CH2:14].C[Si](Cl)(C)C>>[CH2:14]([O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([OH:1])[CH:10]=[C:9]([OH:11])[CH:8]=1)[CH:13]=[CH2:12]Participants
Conditions
- Temperature
- -20 °C
Procedure
To 1.5 g of 3,5-dihydroxybenzoic acid in screw-capped vial was added 10 g of allyl alcohol and the vial was closed and cooled to −20° C. To the cold contents of the reaction vial was added 5 mL of trimethylsilyl chloride via syringe through a septum. The reaction vial was allowed to warm to room temperature and agitated for 16 hours. The vial was opened carefully and its contents transferred to a round-bottomed flask. The solvent was removed under reduced pressure and the residual solid was dried under reduced pressure over potassium hydroxide pellets for 12 h. The semisolid product was used in the subsequent synthetic steps without further purification. The product was analyzed by HPLC and had a retention time of 3.65 on 5 cm C18 reversed phase column with flow rate of 2.5 mL/min of pure acetonitrile (for solvent A) and 0.1% aqueous trifluroacetic acid (for solvent B). The product was characterized by 1H NMR (DMSO-d6, 350 MHz): δ=6.87 (s, 2H, aromatic); 6.44 (s, 1H, aromatic); 5.85-5.96 (m, 1H); 5.16-5.33 (m, 2H); 4.65-4.67(dd, 2H).
Workup
- customthe vial was closed
- temperatureto warm to room temperature
- customits contents transferred to a round-bottomed flask
- customThe solvent was removed under reduced pressure
- dry with materialthe residual solid was dried under reduced pressure over potassium hydroxide pellets for 12 h
- customThe semisolid product was used in the subsequent synthetic steps without further purification
Sources & evidence
- ORD record
- ord-852180b23caa436d9547cead8fa59a70
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435747B2
Reaction notes
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