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

HRID 2367007Notes

Reaction equation

HRID 2367007 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 HCl solution (300 mmol, 100 mL). The reaction was stirred over 2 days after which the reaction was washed using diethyl ether. The aqueous layer was then quenched using NaOH (50%) to obtain a pH of 11. The aqueous layer was extracted using EtOAc (6×300 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo. The reaction was purified via flash chromatography to afford the desired ketone (18 g, 49%). MS (M+H)+ 193.1.

Workup

  1. washwas washed
  2. customThe aqueous layer was then quenched
  3. customto obtain a pH of 11
  4. extractionThe aqueous layer was extracted
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe reaction was purified via flash chromatography

Sources & evidence

ORD record
ord-a487bb31ac974e5a98f5ecc496498952
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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