Nitrogen → HCID 46785010, compound

HRID 82804Notes

Reaction equation

HRID 82804 reaction equation
N#N.[CH3:3][O:4][CH2:5][C:6]1[S:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=1.[BH4-].[Na+].O>CCO.CC(=O)OCC>[CH3:3][O:4][CH2:5][C:6]1[S:10][C:9]([CH2:11][OH:12])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 4311764Sodium borohydrideHCID 13888631HCID 13888631, compound

Product 1

HCID 46785010HCID 46785010, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(methoxymethyl)thiophene-2-carbaldehyde (782 mg, 5.01 mmol) in EtOH (10 mL) was treated at 0° C. with NaBH4 (379 mg, 10.0 mmol) and the resulting solution was stirred for 5 min at 0° C. and then allowed to warm to rt. Water (5 mL) and EA (5 mL) were added. The aq. layer was extracted with EA (2×15 mL) and the combined org. layers were washed with brine, dried over MgSO4, filtered and the solvent was removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.51 min.

Workup

  1. temperatureto warm to rt
  2. extractionThe aq. layer was extracted with EA (2×15 mL)
  3. washlayers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ec815d0a8bb5475abeed72f0cefbc126
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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