Sodium hydride → 5-Ethynyl-1H-indole
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[C:11]C(C)(O)C)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+]>C1(C)C=CC=CC=1>[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)#[CH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 4-(1H-indol-5-yl)-2-methyl-but-3-yn-2-ol (6.6 g, 33.1 mmol), sodiumhydride, 60% in mineral oil (0.13 g, 3.3 mmol) and anhydrous toluene (100 ml) was stirred for 5 hours at 110° C. The crude mixture was evaporated. Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound. Yield 3.44 g (74%). Oil.
Workup
- customThe crude mixture was evaporated
Sources & evidence
- ORD record
- ord-c51de70d132d4025825b45ef3f50f0c6
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662812B2
Reaction notes
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