1-Methoxynaphthalene → HCID 15617937, 화합물

HRID 703917노트

반응식

HRID 703917 반응식
C([Li])CCC.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].[Cl-].[NH4+]>C1CCCCC1>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH3:6]

참가 물질

6

반응물 4

HCID 166681-MethoxynaphthaleneHCID 25517Ammonium ChlorideHCID 813641-Bromo-4-chlorobutaneHCID 178418339Butyllithium

생성물 1

HCID 15617937HCID 15617937, 화합물수율 39%

시약·촉매·용매 1

HCID 8078Cyclohexane용매2회

실험 절차

A solution of N,N,N',N'-tetramethylenediamine (18.12 mL, 0.120 mole) in cyclohexane (36 mL) was treated with n-butyllithium (1.55M in hexane; 79.8 mL, 0.123 mole) at room temperature. A solution of 1-methoxynaphthalene (17.4 mL, 0.120 mole) in cyclohexane (20 mL) was added over 30 minutes, and the resulting solution was stirred for 1.5 hours. It was then cooled to 0°, and 1-bromo-4-chlorobutane (27.0 mL, 0.234 mole) was added over 15 minutes. The mixture was warmed to room temperature and stirred for 17 hours, then poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The crude product was chromatographed with 98:2 hexane/ether to provide the title compound (11.60 g, 39%) as a pale yellow oil.

후처리

  1. temperatureIt was then cooled to 0°
  2. stirringstirred for 17 hours
  3. extractionextracted with ethyl acetate
  4. customThe crude product was chromatographed with 98:2 hexane/ether

출처 및 근거

ORD 기록
ord-355c88f0ad1c48f4adbccaf6c649e74a
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04985435

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