HCID 22490925, compound → HCID 22491008, compound

HRID 2180563Notes

Reaction equation

HRID 2180563 reaction equation
[C:1]([C:5]1[C:14]2[CH:13]=[C:12]([CH:15]=[O:16])[C:11]([O:17][CH2:18][CH3:19])=[CH:10][C:9]=2[C:8]([CH3:21])([CH3:20])[CH2:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:22]([Mg]Cl)[CH3:23]>C1COCC1.CN1CCCN(C)C1=O>[C:1]([C:5]1[C:14]2[CH:13]=[C:12]([CH:15]([OH:16])[CH2:22][CH3:23])[C:11]([O:17][CH2:18][CH3:19])=[CH:10][C:9]=2[C:8]([CH3:20])([CH3:21])[CH2:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 22490925HCID 22490925, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 22491008HCID 22491008, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-tert-butyl-3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalene-2-carbaldehyde (Compound A-27, 450 mg, 1.57 mmol) in THF (7 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 0.3 mL) was added ethylmagnesium chloride (2 M in THF, 1.6 mL, 3.1 mmol). After stirring at 0° C. for 30 min, the reaction was quenched with 1N HCl. The resulting mixture was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound as a colorless oil after purification by flash chromatography (silica gel, 10% ethyl acetate in hexane).

Workup

  1. customthe reaction was quenched with 1N HCl
  2. additionThe resulting mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9aa1a6af77ca4e1f8f9dbe764bfef81a
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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