HCID 23518554, compound → HCID 23518590, compound

HRID 1836872Notes

Reaction equation

HRID 1836872 reaction equation
Br[C:2]1[C:11]([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:10][C:9]2[C:8]([CH3:24])([CH3:23])[CH2:7][CH2:6][C:5]([CH3:26])([CH3:25])[C:4]=2[CH:3]=1.[Cu][C:28]#[N:29]>CN1CCCC1.[OH-].[NH4+]>[C:28]([C:2]1[C:11]([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18])=[CH:10][C:9]2[C:8]([CH3:24])([CH3:23])[CH2:7][CH2:6][C:5]([CH3:26])([CH3:25])[C:4]=2[CH:3]=1)#[N:29]

Participants

5

Reactant 2

HCID 23518554HCID 23518554, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 23518590HCID 23518590, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
175 °C

Procedure

To a solution of 9.0 g (20.5 mmol) of 2-bromo-3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene in 70 mL of N-methyl pyrollidine was added 7.36 g (82 mmol) of copper (I) cyanide and the reaction mixture was heated to 175° C. After 16 hours the reaction mixture was cooled to room temperature and diluted with 10% aqueous ammonium hydroxide. The resulting salts were removed by filtration and washed with hot ethyl acetate. The filtrate was extracted with ethyl acetate and the combined organic fractions were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (gradient elution: 3-25% ethyl acetate/hexane) to give 4.8 g (61%) of 2-cyano-3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene.

Workup

  1. temperatureAfter 16 hours the reaction mixture was cooled to room temperature
  2. customThe resulting salts were removed by filtration
  3. washwashed with hot ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (gradient elution: 3-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c9dda8c341c34ec789d7e03813b3095a
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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