Ammonium Chloride → 7-(Diphenylmethoxy)-1H-indole
Reaction equation
[CH:1]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([Mg]Br)=[CH2:25].[Cl-].[NH4+]>O1CCCC1>[CH:1]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:16]=1[NH:21][CH:25]=[CH:24]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
11.95 mmol of the compound obtained in Step A above are dissolved, under an inert atmosphere, in 80 ml of anhydrous tetrahydrofuran. The temperature of the reaction mixture is then lowered to −40° C. and then 41.84 mmol of a 1M solution of vinylmagnesium bromide in tetrahydrofuran are added dropwise to the solution, which is then stirred for 2 hours 50 minutes from −40° C. to 0° C. The reaction mixture is then hydrolysed at 0° C. using 100 ml of a saturated aqueous ammonium chloride solution, and the aqueous phase is extracted three times with ethyl acetate. The organic phases are combined, dried over magnesium sulphate, filtered and evaporated. Purification by flash chromatography over silica gel (petroleum ether/ethyl acetate: 9/1) allows the expected product to be isolated.
Workup
- customis then lowered to −40° C.
- customhydrolysed at 0° C.
- extractionthe aqueous phase is extracted three times with ethyl acetate
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- customevaporated
- customPurification by flash chromatography over silica gel (petroleum ether/ethyl acetate: 9/1)
- customto be isolated
Sources & evidence
- ORD record
- ord-ec4cca4f16c2406583ef840a41861f94
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202255B2
Reaction notes
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