Nitrogen → HCID 54333605, 화합물

HRID 1744002노트

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HRID 1744002 반응식
N#N.Br[C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C:7]([O:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[CH:6][CH:5]=1.C([Li])CCC.[B:25](OCC)([O:29]CC)[O:26]CC>O1CCCC1>[CH3:18][N:17]([CH2:16][CH2:15][O:14][C:7]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[C:4]([B:25]([OH:29])[OH:26])=[CH:5][CH:6]=1)[CH3:19]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 9009Triethyl borateHCID 22236436HCID 22236436, 화합물HCID 178418339Butyllithium

생성물 1

HCID 54333605HCID 54333605, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

To a 1 L 3N round-bottomed flask equipped with septum and N2 inlet were added 8.55 g (28.7 mmol) 4-bromo-1-(2-dimethylaminoethoxy)-5,6,7,8-tetrahydro-naphthalene and 300 mL dry tetrahydrofuran. The solution was cooled to −70° C., and 13.8 mL (34.4 mmol) of a 2.5 M solution of butyl lithium in hexanes was added. The reaction was stirred at −70° C. for 1 h, then 5.9 mL (34.4 mmol) triethyl borate was added, and the reaction stirred at −70° C. for 2 h and warmed to room temperature overnight. The reaction was quenched with aqueous saturated ammonium chloride solution and extracted three times with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was triturated with hexane to a white solid, 6.3 g (83.5%).

후처리

  1. stirringthe reaction stirred at −70° C. for 2 h
  2. temperaturewarmed to room temperature overnight
  3. customThe reaction was quenched with aqueous saturated ammonium chloride solution
  4. extractionextracted three times with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was triturated with hexane to a white solid, 6.3 g (83.5%)

출처 및 근거

ORD 기록
ord-245ebe5e16d64e71bd70110f079e6672
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07012078B2

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