Tetrahydrofuran → HCID 59774805, compound

HRID 2387282Notes

Reaction equation

HRID 2387282 reaction equation
[H-].[Na+].O1CCCC1.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=2)[CH:10]=[CH:9]1.[CH2:19]([S:22](Cl)(=[O:24])=[O:23])[CH2:20][CH3:21]>>[CH2:19]([S:22]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)(=[O:24])=[O:23])[CH2:20][CH3:21]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 662791-Propanesulfonyl chlorideHCID 27734351H-Indole-6-carboxaldehyde

Product 1

HCID 59774805HCID 59774805, compoundYield 0.1%

Procedure

To sodium hydride (0.174 g, 4.35 mmol) in tetrahydrofuran (6.8 mL, 0.084 mol), 1H-Indole-6-carbaldehyde (59, 0.486 g, 3.35 mol) was added. After 30 minutes, propane-1-sulfonyl chloride (0.565 mL, 5.02 mol) was added. After two hours, it was quenched with 1M HCl (aqueous) and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated. The desired compound was purified by silica gel column chromatography eluting with a gradient of ethyl acetate in hexane to give 516 mg of desired compound. MS (ESI) [M−H+]−=250.1.

Workup

  1. waitAfter two hours
  2. customit was quenched with 1M HCl (aqueous)
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe desired compound was purified by silica gel column chromatography
  9. washeluting with a gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-354d2dfe7e7846bc943689949a6ec33b
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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