Triethylamine → HCID 46785436, compound

HRID 1176180Notes

Reaction equation

HRID 1176180 reaction equation
[CH:1]([C:3]1[S:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1)=O.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:12][N:13]([CH2:1][C:3]1[S:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27734305-Formyl-2-thiopheneboronic acidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 46785436HCID 46785436, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 5-formyl-2-thiopheneboronic acid (500 mg, 3.2 mmol) in DCE (30 mL) was added dimethylamine hydrochloride (520 mg, 6.3 mmol) followed by triethylamine (0.9 mL, 6.5 mmol). The reaction mixture was stirred for 10 min before sodium triacetoxyborohydride (1.36 g, 6.3 mmol) was added in one portion. After the reaction mixture was stirred at room temperature for 5 h, it was quenched with 30 mL of MeOH, stirred briefly, then concentrated under vacuum. Introduction of a CH2Cl2/Et2O mixture to this residue revealed a solid, which was filtered and washed with Et2O. The resulting organic filtrate was concentrated to a viscous oil, which was used without further purification.

Workup

  1. additionwas added in one portion
  2. customit was quenched with 30 mL of MeOH
  3. stirringstirred briefly
  4. concentrationconcentrated under vacuum
  5. filtrationwas filtered
  6. washwashed with Et2O
  7. concentrationThe resulting organic filtrate was concentrated to a viscous oil, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-54fde409a3a44a73bc2f49d11741dd51
Source dataset
uspto-grants-2010_11
Patent number
US07842803B2

Reaction notes

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