Ethylene Oxide → 2-(6-methoxynaphthalen-2-yl)ethanol

HRID 1053789노트

반응식

HRID 1053789 반응식
C([Li])(C)(C)C.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1.[CH2:19]1[O:21][CH2:20]1.[NH4+].[Cl-]>C1COCC1.CCOCC>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:19][CH2:20][OH:21])[CH:16]=[CH:15]2

참가 물질

7

반응물 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 2316102-(6-methoxynaphthalen-2-yl)ethanol수율 53%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

tert-Butyllithium (5.2 mL, 8.84 mmol, 1.7 M/pentane) was added to a −78° C. solution of 2-bromo-6-methoxynaphthalene (1.0471 g, 4.42 mmol) in THF (10 mL)/ether (10 mL). After 30 minutes, a solution of ethylene oxide in THF (2 mL, 23 mmol, 0.5 g/mL) was added and the reaction was allowed to warm to room temperature. After overnight stirring, 30 mL saturated NH4Cl solution was added and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (478 mg, 53%).

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic solution was then dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-b64edfb455f948ada4fcec5d61835174
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394273B2

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