Carbon Dioxide → 1(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

HRID 2609

Reaction equation

HRID 2609 reaction equation
[CH3:1][C:2]1[S:6][C:5]([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:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.CN([CH:33]=[O:34])C.C(=O)=O>C1COCC1.CCOCC>[CH3:1][C:2]1[S:6][C:5]([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:4][CH:3]=1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8003PentaneHCID 186200621-(5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene2×HCID 178418306HCID 178418306, compound

Product 1

HCID 186200661(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (-78° C.) solution of 1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound F, 1.35 g, 4.1 mmol), in THF (20 mL) was added t-BuLi in pentane (1.7M solution, 3.5 mL, 5.95 mmol). The reaction was stirred for 15 minutes and DMF (600 mg, 5.8 mmol) was added and dry-ice cooling was replaced with ice-water bath. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with ether (70 mL) and washed with water (5 mL), brine (5 mL) and dried with MgSO4. Solvent was removed by distillation. The product was purified by silicagel chromatography to afford the title compound as a colorless oil.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 4 hours
  2. washwashed with water (5 mL), brine (5 mL)
  3. dry with materialdried with MgSO4
  4. customSolvent was removed by distillation
  5. customThe product was purified by silicagel chromatography

Sources & evidence

ORD record
ord-4955e9d4488f4c70a01e631513107eb7
Source dataset
uspto-grants-1998_03
Patent number
US05728846

Linked notes

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