Water → HCID 69253549, compound

HRID 2224619Notes

Reaction equation

HRID 2224619 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[CH3:22][Si:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][O:26][CH2:27]Cl.O>O1CCCC1>[I:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([CH2:27][O:26][CH2:25][CH2:24][Si:23]([CH3:30])([CH3:29])[CH3:22])[S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1379399HCID 1379399, compoundHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 69253549HCID 69253549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of sodium hydride (1.17 g, 29.25 mmol, 60% in oil) in anhydrous tetrahydrofuran (40 mL), which had been cooled to 0° C., was added N-(2-iodophenyl)-4-methoxybenzenesulfonamide (9.36 g, 19.6 mmol) in tetrahydrofuran (20 mL). After the addition was complete, the cooling bath was removed and the mixture stirred at room temperature for 90 minutes. 2-(Trimethylsilyl)ethoxymethyl chloride (4.25 g, 25.5 mmol) in tetrahydrofuran (20mL) was added dropwise and the reaction mixture stirred for an additional 16 hours. Water (10 mL) was added and the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was washed with a saturated, aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the organic phase was filtered and the filtrate was evaporated in vacuo to yield the crude title compound as a colorless oil. Purification by silica gel chromatography by elution with hexane-ethyl acetate (10:1) provided the title compound as a colorless oil. Trituration with hexane provided the title compound as a white solid (8.55 g, 16.5 mmol, 84%), m.p. 69-70° C.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. stirringthe reaction mixture stirred for an additional 16 hours
  4. concentrationthe mixture was concentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic phase was washed with a saturated, aqueous sodium chloride solution
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. filtrationthe organic phase was filtered
  9. customthe filtrate was evaporated in vacuo
  10. customto yield the crude title compound as a colorless oil
  11. customPurification by silica gel chromatography
  12. washby elution with hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-a18fc24a2c38454aaf6aee0b42a8eaa9
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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