Hydrochloric Acid → HCID 18630308, compound

HRID 1276704Notes

Reaction equation

HRID 1276704 reaction equation
C[N:2]([CH2:4][CH2:5]N(C)C)C.[Li]C(CC)C.[CH2:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CO[B:22]([O:25]C)OC.[ClH:27].[C:28]([O-:31])(O)=O.[Na+]>C1COCC1>[Cl:27][C:14]1[C:19]2[C:28](=[O:31])[N:2]([CH2:4][CH3:5])[B:22]([OH:25])[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 8470Trimethyl borateHCID 516892Sodium BicarbonateHCID 178418400CID 53628100

Product 1

HCID 18630308HCID 18630308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example f (5.0 g, 27.2 mmol), TMEDA (6.6 g, 57.1 mmol), and THF (100 Ml) were stirred at -78° C. under nitrogen, and 1.3M s-BuLi in cyclohexane (44 mL, 57.1 mmol) was added dropwise. The mixture was stirred for 15 min and trimethylborate (3.1 g, 29.9 mmol) was added all at once. The mixture was then stirred at -78° C. for 30 min before warming to RT. It was then poured into 10% HCl (100 mL). This mixture was made basic with sat aq NaHCO3 and extracted with ether. The aq layer was reacidified and extracted with CH2Cl2. The combined organic layers were dried (MgSO4), concentrated, and recrystallized to yield 4.2 g 4-chloro-2-ethyl-1-hydroxy-1H-2,1-benzazaborol-3(2H)-one as a white solid. m.p. 210-211° C.

Workup

  1. stirringThe mixture was then stirred at -78° C. for 30 min
  2. extractionextracted with ether
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. customrecrystallized

Sources & evidence

ORD record
ord-a993c035852946d59fcb544ca192d9bc
Source dataset
uspto-grants-2000_12
Patent number
US06166057

Reaction notes

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