Carbon Dioxide → 1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

HRID 1862729Notes

Reaction equation

HRID 1862729 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:3][CH:2]=1.[Li]C(C)(C)C.CCCCC.CN(C)[CH:33]=[O:34].C(=O)=O>C1COCC1.C(OC(=O)C)C>[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:33]=[O:34])[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8003PentaneHCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene2×HCID 178418306HCID 178418306, compound

Product 1

HCID 865886771-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (−78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid.

Workup

  1. washwashed with water (15 mL)
  2. dry with materialThe organic layer was dried with MgSO4 and solvent
  3. customwas removed under reduced pressure
  4. customThe crude material was purified by silicagel chromatography

Sources & evidence

ORD record
ord-5cebc8cde7e34df1b9f8aaa58feaa128
Source dataset
uspto-grants-2003_03
Patent number
US06538149B1

Reaction notes

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