Sodium hydride → HCID 66914783, compound

HRID 880453Notes

Reaction equation

HRID 880453 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([I:19])[CH:16]=[C:15]2[CH2:20][OH:21])(=O)=O)=CC=1.[H-].[Na+]>O1CCCC1>[I:19][C:17]1[CH:16]=[C:15]2[N:14]([CH:18]=1)[CH2:13][CH2:12][O:21][CH2:20]2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86654671HCID 86654671, compound

Product 1

HCID 66914783HCID 66914783, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[2-(hydroxymethyl)-4-iodo-pyrrol-1-yl]ethyl 4-methylbenzenesulfonate (2.0 g, 4.79 mmol) in tetrahydrofuran (15 mL) was slowly added to a suspension of sodium hydride (120 mg, 60% dispersion in mineral oil; 4.75 mmol) in tetrahydrofuran (5 mL) and stirred at room temperature for 36 h. The reaction was quenched with water and extracted with diethyl ether. The combined organic phases were washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue which was purified by column chromatography over silica gel using 2% ethyl acetate in petroleum ether to afford 7-iodo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine (800 mg, 66%) as a colorless crystalline solid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with diethyl ether
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue which
  7. customwas purified by column chromatography over silica gel using 2% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-b9c482dfbfa34a629cb3a75f75e7309d
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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