Potassium Carbonate → Tert-butyl {2-[(1-ethylnaphthalen-2-yl)oxy]ethyl}carbamate

HRID 1400309

反応式

HRID 1400309 の反応式
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].CCCCCC.C(OCC)(=O)C>C(#N)C>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:2]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 30149752-Naphthol, 1-ethyl-2 回HCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 21226206Ethyl acetate hexane

生成物 1

HCID 86709756Tert-butyl {2-[(1-ethylnaphthalen-2-yl)oxy]ethyl}carbamate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 1-ethylnaphthalen-2-ol (780 mg, 4.53 mmol) and K2CO3 (626 mg, 4.53 mmol) in 15 mL of acetonitrile was added tert-butyl (2-bromoethyl)carbamate (1.015 g, 4.53 mmol). The resulting mixture was heated at reflux overnight. After TLC control (n-hexane/ethyl acetate 7:3) showed the disappearance of 1-ethylnaphthalen-2-ol, solvent was evaporated in vacuo and the residue was dissolved in 15 mL of ethyl acetate and washed with water (3×5 mL), brine (5 mL) and dried over Na2SO4. The evaporation of solvent afforded tert-butyl {2-[(1-ethylnaphthalen-2-yl)oxy]ethyl}carbamate which was dissolved in 10 mL of 4M HCl in dioxane and stirred for 1 h. The solvent was removed under vacuum and the residue was diluted with n-hexane (20 mL) and triturated at room temperature for 2 h. The solid was filtered and dried under vacuum at 50° C. to afford 2-[(1-ethylnaphthalen-2-yl)oxy]ethanaminium chloride as brown solid (821 mg, 72% yield). To a solution of 2-[(1-ethylnaphthalen-2-yl)oxy]ethanaminium chloride (100 mg, 0.397 mmol) in 10 mL of MeOH, K2CO3 (65 mg, 0.47 mmol) was added. After 10 min, 48 μL (0.58 mmol) of furan-2-carbaldehyde were added. The resulting solution was stirred for 1 h at room temperature, added with sodium borohydride (15 mg, 0.397 mmol) and allowed to stir for further 2 h at room temperature. The solvent was evaporated under vacuum. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 97:3) to afford 2-[(1-ethylnaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamine as a brown solid (91 mg, 78% yield).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customwas evaporated in vacuo
  4. dissolutionthe residue was dissolved in 15 mL of ethyl acetate
  5. washwashed with water (3×5 mL), brine (5 mL)
  6. dry with materialdried over Na2SO4
  7. customThe evaporation of solvent

出典と根拠

ORDレコード
ord-1333dd88741d4e799e7639e5d19fdb9d
出典データセット
uspto-grants-2014_12
特許番号
US08906946B2

関連ノート

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