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

HRID 1400309

반응식

HRID 1400309 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1333dd88741d4e799e7639e5d19fdb9d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906946B2

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