Sodium periodate → HCID 67264326, compound

HRID 1041693Notes

Reaction equation

HRID 1041693 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH2:7]([N:9]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][CH2:12][C:11](CO)([OH:23])[CH2:10]1)[CH3:8]>CC(C)=O.O.O1CCCC1>[CH2:7]([N:9]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][CH2:12][C:11](=[O:23])[CH2:10]1)[CH3:8]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67263463HCID 67263463, compound

Product 1

HCID 67264326HCID 67264326, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (0.454 g, 2.12 mmol) was added to 9-Ethyl-7-hydroxymethyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ol (0.114 g, 0.425 mmol) in Acetone (15 mL) and Water (5 mL). After 1 h, the heterogenous mixture was further diluted with Water (10 mL) and Tetrahydrofuran (10 mL), which did not create a homogenous mixture. The mixture was stirred overnight, then was partitioned between water and DCM. Extraction with DCM and washing with brine, followed by drying gave 9-Ethyl-2-nitro-8,9-dihydro-5-oxa-9-aza-benzocyclohepten-7-one (74 mg, 74%). 1H-NMR (CDCl3): 7.69 (s, 1H), 7.62 (d, 1H, J=8.8 Hz), 7.02 (d, 1H, J=8.8 Hz), 4.61 (s, 2H), 4.10 (s, 2H), 3.42 (q, 2H, J=7.2 Hz), 1.26 (t, 3H, J=7.2 Hz).

Workup

  1. customwas partitioned between water and DCM
  2. extractionExtraction with DCM
  3. washwashing with brine
  4. customby drying

Sources & evidence

ORD record
ord-d631339c8d9340ec82440be6853a7ae3
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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