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

HRID 1053789ノート

反応式

HRID 1053789 の反応式
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

参加物

7

反応物 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 2316102-(6-methoxynaphthalen-2-yl)ethanol収率 53%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b64edfb455f948ada4fcec5d61835174
出典データセット
uspto-grants-2016_07
特許番号
US09394273B2

反応ノート

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