t-Butyl bromide → Ethyl 2-(tert-butoxy)-2-(3-phenyl-1-benzothiophen-2-yl)acetate

HRID 590962Notes

Reaction equation

HRID 590962 reaction equation
[OH:1][CH:2]([C:8]1[S:9][C:10]2[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=2[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:23](Br)([CH3:26])([CH3:25])[CH3:24]>C1CCCCC1.[Ag-]=O>[C:23]([O:1][CH:2]([C:8]1[S:9][C:10]2[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=2[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 10485t-Butyl bromideHCID 70813755Ethyl 2-hydroxy-2-(3-phenyl-1-benzothiophen-2-yl)acetate

Product 1

HCID 70813797Ethyl 2-(tert-butoxy)-2-(3-phenyl-1-benzothiophen-2-yl)acetateYield 11%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of ethyl 2-hydroxy-2-(3-phenyl-1-benzothiophen-2-yl)acetate (3b) (340 mg, 1.09 mmol), silver (I) oxide (758 mg, 3.27 mmol) and tertbutylbromide (612 μL, 5.45 mmol) in cyclohexane (20 mL) was vigorously stirred for 48 hours under a nitrogen atmosphere. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired ether oxide (3c) as a white solid (45 mg, 0.12 mmol, 11%).

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 90/10)

Sources & evidence

ORD record
ord-4e097efe176d4f4da38844a66a615b54
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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