[2-(6-Methoxy-quinazolin-4-yl)-ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol → 4-Hydroxy-4-[2-(6-methoxyquinazolin-4-yl)-ethyl]cyclohexanone

HRID 1354207Notes

Reaction equation

HRID 1354207 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[CH2:13][CH2:14][CH:15]1[CH2:19]OC2(CCC(O)CC2)[O:16]1>CC(O)=O.C1COCC1.O>[OH:16][C:15]1([CH2:14][CH2:13][C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH2:19][CH2:4][C:3](=[O:2])[CH2:12][CH2:11]1

Participants

3

Reactant 1

HCID 86603231[2-(6-Methoxy-quinazolin-4-yl)-ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol

Product 1

HCID 211046484-Hydroxy-4-[2-(6-methoxyquinazolin-4-yl)-ethyl]cyclohexanone

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of 8-([2-(6-methoxy-quinazolin-4-yl)-ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol (0.623 g, 1.81 mmol) in AcOH/THF/H2O (3/2/2, 10 ml) was stirred at 60° C. for 30 hours. The reaction mixture was concentrated to dryness by rotary evaporation. The residue was diluted with sodium bicarbonate (100 ml) and ethyl acetate (100 ml), the phases were separated and the aqueous phase was extracted twice using 50 ml of ethyl acetate each time. The combined organic phases were dried over MgSO4, filtered and concentrated to dryness by rotary evaporation.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness by rotary evaporation
  2. additionThe residue was diluted with sodium bicarbonate (100 ml) and ethyl acetate (100 ml)
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted twice
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-c20cf818732b4141af723199b7b09873
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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