2-Nitropropane → 3-Fluoro-2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene

HRID 1836884Notes

Reaction equation

HRID 1836884 reaction equation
[N+](C(C)C)([O-])=[O:2].[Na].[F:8][C:9]1[C:18]([CH2:19]Br)=[CH:17][C:16]2[C:15]([CH3:22])([CH3:21])[CH2:14][CH2:13][C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1>C(O)C>[F:8][C:9]1[C:18]([CH:19]=[O:2])=[CH:17][C:16]2[C:15]([CH3:22])([CH3:21])[CH2:14][CH2:13][C:12]([CH3:24])([CH3:23])[C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 234988892-Fluoro-3-bromomethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 234989783-Fluoro-2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthaleneYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5.26 g (59.0 mmol) of 2-nitropropane was added to a solution prepared by dissolving 1.04 g (45.4 mmol) of sodium in 60 mL of ethanol. The resulting solution was added to a solution of 16.9 g (45.4 mmol) of crude 2-fluoro-3-bromomethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 60 mL of ethanol. After 5 hours the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1M aqueous sodium hydroxide, water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by flash chromatography on silica gel (1% ethyl acetate/hexane) to afford 6.17 g (58%) of 3-fluoro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde (m.p.=119.4-120.0° C.).

Workup

  1. customprepared
  2. customAfter 5 hours the reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1M aqueous sodium hydroxide, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography on silica gel (1% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6acc282be1a449eb8c6ed8231e07f8aa
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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