Triethylamine → HCID 23498918, compound

HRID 1836897Notes

Reaction equation

HRID 1836897 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:8]([CH3:14])([CH3:13])[CH:7]([O:15][C:16](=[O:18])[CH3:17])[CH2:6][C:5]([CH3:20])([CH3:19])[C:4]=2[CH:3]=1.COC([SiH3])=C(OC)OC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N([CH2:57][CH3:58])CC)C.[CH2:59]([O:61][C:62](=[O:70])[C:63]1[CH:68]=[CH:67][C:66](Br)=[CH:65][CH:64]=1)[CH3:60].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN1CCCC1.[Cl-].[Na+].O>[CH2:59]([O:61][C:62](=[O:70])[C:63]1[CH:68]=[CH:67][C:66](/[CH:57]=[CH:58]/[C:2]2[C:11]([CH3:12])=[CH:10][C:9]3[C:8]([CH3:14])([CH3:13])[CH:7]([O:15][C:16](=[O:18])[CH3:17])[CH2:6][C:5]([CH3:20])([CH3:19])[C:4]=3[CH:3]=2)=[CH:65][CH:64]=1)[CH3:60]

Participants

9

Reactant 6

HCID 8471Triethylamine2×HCID 22043Ethyl 4-bromobenzoateHCID 80271Tri-o-tolylphosphineHCID 2724141Tetrabutylammonium FluorideHCID 23498938HCID 23498938, compoundHCID 91996421HCID 91996421, compound

Product 1

HCID 23498918HCID 23498918, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1 g (3 mmol) of 2-bromo-3-methyl-6-acetoxy -5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene, 0.68 ml (4.42 mmol) of trimethoxyvinyl silane, 0.12 g (0.53 mmol), 0.36 g of Tri-o-tolylphosphine (1.2 mmol) and 0.82 mL of triethylamine (5.9 mmol) in 10 mL of N-methyl pyrollidine was heated at 90° C. After 3 hours, the reaction was cooled to room temperature and 0.57 mL (3.5 mmol) of ethyl4-bromobenzoate, 0.82 mL of triethylamine (5.9 mmol) and 5 mL (5 mmol) of tetrabutylammonium fluoride were added. The reaction mixture was heated to 90° again. After 2.5 hours, the reaction was cooled to room temperature, poured into brine and extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution 2-5% ethyl acetate/hexane) to afford 0.2 g (20%) of Ethyl-4-[(E)-2-(5,5,8,8-Tetramethyl-3-methyl-6-acetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate (M+=434).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. temperatureThe reaction mixture was heated to 90° again
  3. waitAfter 2.5 hours
  4. temperaturethe reaction was cooled to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (gradient elution 2-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cf4561a7d5c344e5947adbd4c625f52a
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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