Dimethyl Sulfoxide → HCID 22033007, compound

HRID 1792366Notes

Reaction equation

HRID 1792366 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=2)[O:14][CH2:13][C:12]1([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=1)[CH3:25].CS(C)=O.[N-:40]=[N+:41]=[N-:42].[Na+].CCCCCC>C(OCC)(=O)C>[N:40]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=2)[O:14][CH2:13][C:12]1([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=1)[CH3:25])=[N+:41]=[N-:42]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8058HexaneHCID 33557Sodium AzideHCID 22033087HCID 22033087, compound

Product 1

HCID 22033007HCID 22033007, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To (3RS,4RS)-4-(9-bromo-5-oxanonyl)-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (276 mg, 0.5 mmol) in. DMSO was added sodium azide (65.1 mg, 1 mmol). The mixture was stirred at 80° C. for 3 h. After cooling, the mixture was extracted with ethyl acetate, dried over MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the concentrate thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=10:1) to give 269 mg (yield. 100%) of a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. concentrationthe concentrate thus
  7. customobtained
  8. customto give
  9. custom269 mg (yield. 100%) of a colorless oil

Sources & evidence

ORD record
ord-0b5f43cf482f48e3aeb92b00209f2216
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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