Sodium Carbonate → HCID 59556171, compound

HRID 1809926Notes

Reaction equation

HRID 1809926 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]2([OH:17])[CH2:16][CH2:15][C:10]3(OCC[O:11]3)[CH2:9][CH2:8]2)[CH:4]=[N:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[OH:17][C:7]1([C:5]2[CH:4]=[N:3][CH:2]=[N:1][CH:6]=2)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 59556106HCID 59556106, compound

Product 1

HCID 59556171HCID 59556171, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-pyrimidin-5-yl-1,4-dioxaspiro[4,5]decan-8-ol (0.14 g, 0.59 mmol) in 10 mL of THF/1 N HCl (1:1) was stirred for 24 h at room temperature. The mixture was treated with Na2CO3 to pH 8 and extracted with EtOAc (3×). The combined organic layers were washed with saturated NaCl solution, dried (MgSO4), and concentrated to give 0.11 g of 4-hydroxy-4-pyrimidin-5-ylcyclohexanone in 79% yield. MS (EI) calcd: (M+H)+=192.1. Found: 192.1.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with saturated NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dd5f0edadac743259fd81500df5ab74f
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

Loading…