Pyrazole → HCID 23498931, compound

HRID 1836917Notes

Reaction equation

HRID 1836917 reaction equation
CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[NH:25]1[CH:29]=[CH:28][CH:27]=[N:26]1.[Br:30][C:31]1[C:40]([CH2:41]Br)=[CH:39][C:38]2[C:37]([CH3:44])([CH3:43])[CH2:36][CH2:35][C:34]([CH3:46])([CH3:45])[C:33]=2[CH:32]=1>O1CCCC1>[Br:30][C:31]1[C:40]([CH2:41][N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)=[CH:39][C:38]2[C:37]([CH3:44])([CH3:43])[CH2:36][CH2:35][C:34]([CH3:46])([CH3:45])[C:33]=2[CH:32]=1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 2855718-Crown-6HCID 234989536-Bromo-7-(bromomethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 23498931HCID 23498931, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.955 g (8.52 mmol) of potassium tert-butoxide and 1.877 g (7.10 mmol) 18-crown-6 ether in 35 ml tetrahydrofuran was added 0.580 g (8.52 mmol) pyrazole. After 10 minutes 2.557 g (7.10 mmol) 2-bromo-5,5,8,8-tetramethyl-3-bromomethyl-5,6,7,8-tetrahydronaphthalene was added in 15 ml THF. After 17 hours the reaction was concentrated under reduced pressure and acidified with 1M hydrochloric acid. The aqueous solution was extracted with ethyl ether, washed with saturated sodium bicarbonate, water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography (gradient elution with hexane-25% ethyl acetate/hexane) to afford 1.185 g (48%) of 2-bromo-5,5,8,8,-tetramethyl-3-((pyrazol-1-yl)methyl)-5,6,7,8-tetrahydronaphthalene (M+1=348).

Workup

  1. concentrationAfter 17 hours the reaction was concentrated under reduced pressure
  2. extractionThe aqueous solution was extracted with ethyl ether
  3. washwashed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (gradient elution with hexane-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6edf43aad83649aa829b237f8c866ce0
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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