Tetrahydrofuran → HCID 66914783, compound

HRID 2173039Notes

Reaction equation

HRID 2173039 reaction equation
[H-].[Na+].C1COCC1.CC1C=CC(S(O[CH2:19][CH2:20][N:21]2[CH:25]=[C:24]([I:26])[CH:23]=[C:22]2[CH2:27][OH:28])(=O)=O)=CC=1>O>[I:26][C:24]1[CH:23]=[C:22]2[N:21]([CH:25]=1)[CH2:20][CH2:19][O:28][CH2:27]2

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 86654671HCID 86654671, compound

Product 1

HCID 66914783HCID 66914783, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of sodium hydride (0.261 g, 6.53 mmol) and THF (10 mL) was slowly added a solution of 2-(2-(hydroxymethyl)-4-iodo-1H-pyrrol-1-yl)ethyl 4-methylbenzenesulfonate (2.75 g, 6.53 mmol) and THF (25 mL). The reaction mixture was stirred at room temperature for 30 hours, then diluted with water (20 mL) and extracted with EtOAc (2×60 mL). The organic phase was dried over sodium sulfate, evaporated, and purified using silica gel column (80 g) chromatography, eluting with a gradient of 0-100% hexane and EtOAc. The pure compound fractions were combined and evaporated to give the title compound as a tan solid, which turned green on standing (1.02 g, 63%). ESI-MS m/z [M+H]+ calc'd for C7H8INO, 250. found, 250.

Workup

  1. extractionextracted with EtOAc (2×60 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated
  4. custompurified
  5. washeluting with a gradient of 0-100% hexane and EtOAc
  6. customevaporated

Sources & evidence

ORD record
ord-2c7a64e12b4843528e16d7f398fc4399
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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