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Acetone → Tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate

HRID 454641
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HRID 454641 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9]Cl.CC(C)=O.[OH:15][C:16]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][C:17]=1[C:18]([NH:20][C:21]1[CH:33]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19]>C(OCC)(=O)C.O>[CH3:7][O:8][CH2:9][O:15][C:16]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][C:17]=1[C:18]([NH:20][C:21]1[CH:33]=[C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19]
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참가 물질

7

반응물 4

HCID 180AcetoneHCID 7864Chloromethyl Methyl Ether3회HCID 11430Potassium Carbonate3회HCID 58508560Tert-butyl 2-(2-hydroxy-5-methylbenzamido)-4-phenylbenzoate

생성물 1

HCID 66991033Tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (0.51 g) and methoxymethyl chloride (0.23 mL) were sequentially added to an acetone (9.0 mL) suspension of tert-butyl 2-(2-hydroxy-5-methylbenzamido)-4-phenylbenzoate (0.60 g), followed by stirring at room temperature for 1 hour and 30 minutes. Potassium carbonate (0.21 g) and methoxymethyl chloride (0.11 mL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 2 hours. Potassium carbonate (0.51 g) and methoxymethyl chloride (0.23 mL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 2 hours and then heating to reflux for 20 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-80% hexane/ethyl acetate] to obtain 0.64 g of tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate.

후처리

  1. stirringby stirring at room temperature for 2 hours
  2. stirringby stirring at room temperature for 2 hours
  3. temperatureheating
  4. temperatureto reflux for 20 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-80% hexane/ethyl acetate]

출처 및 근거

ORD 기록
ord-491b5827e9324172984a4fd862c39e71
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492582B2

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