Nitrogen → (5-Methanesulfonyl-furan-2-yl)-methanol

HRID 2064943Notes

Reaction equation

HRID 2064943 reaction equation
N#N.C([O:5][C:6]([C:8]1[O:9][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][CH:12]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:16][S:13]([C:10]1[O:9][C:8]([CH2:6][OH:5])=[CH:12][CH:11]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 947NitrogenHCID 14487Diisobutylaluminum hydrideHCID 600069435-Methanesulfonyl-furan-2-carboxylic acid ethyl ester

Product 1

HCID 59826884(5-Methanesulfonyl-furan-2-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-methanesulfonyl-furan-2-carboxylic acid ethyl ester (1.26 g) in THF (57.0 mL) was treated at −78° C. with DiBAL (19.50 mL of a 1M solution in THF, 19.50 mmol) and the reaction mixture was stirred at this temperature for 2 h. The reaction mixture was poured on Rochelle's salt (100 mL) and stirred at rt for 12 h. The aq. layer was extracted with EA (2×100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (30:70 hept-EA) gave the title compound as a yellow oil. TLC: rf (30:70 hept-EA)=0.28. LC-MS-conditions 02: tR=0.50 min.

Workup

  1. additionThe reaction mixture was poured on Rochelle's salt (100 mL)
  2. stirringstirred at rt for 12 h
  3. extractionThe aq. layer was extracted with EA (2×100 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (30:70 hept-EA)

Sources & evidence

ORD record
ord-f3d799879429407389aea7192e7d6245
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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