t-Butyl bromide → ethyl 2-(tert-butoxy)-2-(1-phenyl-1H-indol-2-yl)acetate

HRID 590968Notes

Reaction equation

HRID 590968 reaction equation
[OH:1][CH:2]([C:8]1[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:23](Br)([CH3:26])([CH3:25])[CH3:24]>C1CCCCC1.ClCCl.[Ag-]=O>[C:23]([O:1][CH:2]([C:8]1[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 2

HCID 10485t-Butyl bromideHCID 70813712ethyl 2-hydroxy-2-(1-phenyl-1H-indol-2-yl)acetate

Product 1

HCID 70813717ethyl 2-(tert-butoxy)-2-(1-phenyl-1H-indol-2-yl)acetateYield 33.5%

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalystHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

A mixture of ethyl 2-hydroxy-2-(1-phenyl-1H-indol-2-yl)acetate (5b) (50 mg, 0.17 mmol), silver (I) oxide (130 mg, 0.56 mmol) and tertbutylbromide (114 μL, 1.02 mmol) in cyclohexane (4 mL) and dichloromethane (2 mL) was vigorously stirred for 24 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5) to afford the desired ether oxide (5c) as a white solid (20 mg, 0.057 mmol, 33%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-0417813cc9364e73b8888f67d7baddea
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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