Hydrochloric Acid → 4-Hydroxy-4-pyrimidin-2-yl-cyclohexanone

HRID 969567Notes

Reaction equation

HRID 969567 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1([OH:17])[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1.Cl>C1COCC1>[OH:17][C:7]1([C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 590174338-Pyrimidin-2-yl-1,4-dioxa-spiro[4.5]decan-8-ol

Product 1

HCID 590174304-Hydroxy-4-pyrimidin-2-yl-cyclohexanoneYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product from step A (190 mmol, 44 g) in THF (200 mL) was added aqueous HCl solution (300 mmol, 100 mL). The reaction was stirred over 2 days and extracted using diethyl ether. The aqueous layer was then neutralized using aqueous NaOH (50%) to obtain a pH of 11 and extracted using EtOAc (6×300 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo. The residue was purified via flash chromatography on silica to afford the desired ketone (18 g, 49%). MS (M+H)+193.1.

Workup

  1. extractionextracted
  2. customto obtain a pH of 11
  3. extractionextracted
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via flash chromatography on silica

Sources & evidence

ORD record
ord-b9910094fa1441c2bad9ff9976190b46
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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