Sodium Thiosulfate → HCID 83646766, compound

HRID 1051953Notes

Reaction equation

HRID 1051953 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH:9]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+].C1COCC1.[OH2:36]>>[Br:8][CH:10]1[C:11](=[O:36])[CH2:12][CH2:13][CH2:14][CH:9]1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 5

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 11007985Methyl cyclohex-2-ene-1-carboxylateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 83646766HCID 83646766, compound

Procedure

At 0° C., NBS (9.08 g, 51.0 mmol) was added to a soln. of methyl cyclohex-2-enecarboxylate (5.96 g, 42.5 mmol) [Bioorg. Med. Chem. 1999, 7, 1505-1511.] in THF/H2O (500 mL, 9:1). The mixture was allowed to warm to RT and stirred for 2 h. Subsequently, aq. sat. Na2S2O3 and aq. sat. NaHCO3 were added and the mixture was conc. in vacuo. The residue was partitioned between EtOAc and aq. sat. NaHCO3. The org. layer was washed multiple times with aq. sat. NaHCO3 and brine, dried over MgSO4, and conc. in vacuo.

Workup

  1. customThe residue was partitioned between EtOAc and aq. sat. NaHCO3
  2. washlayer was washed multiple times with aq. sat. NaHCO3 and brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-eef3c608dc9d438bab9897eb04eda02f
Source dataset
uspto-grants-2016_07
Patent number
US09388198B2

Reaction notes

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