Hydrochloric Acid → HCID 59030615, compound

HRID 1619199Notes

Reaction equation

HRID 1619199 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1([CH2:17][OH:18])[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1.Cl>C1COCC1>[OH:18][CH2:17][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 59030571HCID 59030571, compound

Product 1

HCID 59030615HCID 59030615, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]dec-8-yl)-methanol (295 mg, 1.18 mmol) in THF (10 mL) was added 3 N aqueous HCl (10 mL) at 25° C. After being stirred at 25° C. for 24 h, THF was removed under reduced pressure and the reaction was neutralized (saturate aqueous NaHCO3) and extracted (4×10% MeOH/DCM). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to provide 4-(hydroxymethyl)-4-(pyrimidin-2-yl)cyclohexanone (238 mg, 1.15 mmol, 98%) as a pale yellow solid.

Workup

  1. customTHF was removed under reduced pressure
  2. concentration(saturate aqueous NaHCO3)
  3. extractionextracted (4×10% MeOH/DCM)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2f325b9b0654020b3c1715ff0e82cfc
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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