Dimethyl Sulfide → tert-Butyl[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl](2-oxoethyl)carbamate

HRID 1466058Notes

Reaction equation

HRID 1466058 reaction equation
[CH2:1]([N:4]([CH2:12][CH2:13][C:14]1[CH:23]=[CH:22][C:17]2[C:18](=[O:21])[O:19][CH2:20][C:16]=2[CH:15]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=C.[O:24]=[O+][O-].CSC>CO.CCOC(C)=O>[O:21]=[C:18]1[C:17]2[CH:22]=[CH:23][C:14]([CH2:13][CH2:12][N:4]([CH2:1][CH:2]=[O:24])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[CH:15][C:16]=2[CH2:20][O:19]1

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 117599278tert-Butyl allyl[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]carbamate

Product 1

HCID 117599267tert-Butyl[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl](2-oxoethyl)carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl allyl[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]carbamate (0.58 g, 1.8 mmol) in MeOH (50 mL) was bubbled ozone until it turned blue. Nitrogen was bubbled through the solution to remove excess ozone, which was followed by addition of dimethyl sulfide (1.4 mL, 18 mmol). The solution was allowed to warm up slowly. The mixture was diluted with EtOAc, washed with brine, dried over sodium sulfate, and concentrated to afford the product. The crude material was used directly in the next step without further purification.

Workup

  1. customNitrogen was bubbled through the solution
  2. customto remove excess ozone, which
  3. temperatureto warm up slowly
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford the product
  8. customThe crude material was used directly in the next step without further purification

Sources & evidence

ORD record
ord-379bbd420eb04e69a85957af660ecf37
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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