Acetaldehyde → HCID 67263706, compound

HRID 1686918Notes

Reaction equation

HRID 1686918 reaction equation
C(O[BH-](O[C:11](=[O:13])[CH3:12])OC(=O)C)(=O)C.[Na+].[N+:15]([C:18]1[CH:19]=[C:20]2[C:26](=[CH:27][CH:28]=1)[CH:25]1O[CH:21]2[CH2:22][NH:23][CH2:24]1)([O-:17])=[O:16].C(=O)C.ClC(Cl)C>C(O)(=O)C>[CH2:22]([N:23]1[CH2:12][CH:11]2[O:13][CH:25]([C:26]3[C:20]2=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:28][CH:27]=3)[CH2:24]1)[CH3:21]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 67264550HCID 67264550, compound

Product 1

HCID 67263706HCID 67263706, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium triacetoxyborohydride (530 mg, 2.5 mmol) was added to a solution of 4-nitro-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (200 mg, 0.97 mmol), acetaldehyde (0.15 mL, 2.5 mmol), acetic acid (0.1 mL) and dichloroethane (5 mL). The reaction was stirred at room temperature for 5 h. The reaction was then quenched with saturated aqueous NaHCO3 (10 mL), extracted with CH2Cl2 (2×10 mL), dried over MgSO4, filtered, and concentrated. The remaining residue was purified with silica gel chromatography (10-100% EtOAc in hexanes) to give 10-Ethyl-4-nitro-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene as a yellow oil (115 mg, 51%). MS (m/e) 235 (M+1).

Workup

  1. customThe reaction was then quenched with saturated aqueous NaHCO3 (10 mL)
  2. extractionextracted with CH2Cl2 (2×10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe remaining residue was purified with silica gel chromatography (10-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-539e3badd04948dfb22bd5b8c715e3e5
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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