Sodium Bicarbonate → 5-[2-(2-Chloro-4-methoxy-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one

HRID 2096861노트

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HRID 2096861 반응식
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11](Cl)=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:14].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[Cl:25].C([O-])(O)=O.[Na+]>COCCOC.[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:18]1[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=1[CH2:16][C:11]([C:8]1[CH:9]=[CH:10][C:5]2[O:4][C:3](=[O:14])[N:2]([CH3:1])[C:6]=2[CH:7]=1)=[O:12]

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 104431423-Methyl-2-oxo-1,3-benzoxazole-5-carbonyl chlorideHCID 223274281-(Bromomethyl)-2-chloro-4-methoxybenzene

생성물 1

HCID 666970405-[2-(2-Chloro-4-methoxy-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one수율 55%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매3회

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온도
0 °C

실험 절차

To a suspension of zinc powder (1.67 g) in 1,2-dimethoxyethane (60 mL) was added tetrakis(triphenylphosphine)palladium(0) (295 mg). A suspension of the 3-methyl-2-oxo-2,3-dihydro-benzooxazole-5-carbonyl chloride (2.71 g) in 1,2-dimethoxyethane (60 mL) was slowly added over a period of 20 minutes. The mixture was cooled in an ice bath and a solution of 1-bromomethyl-2-chloro-4-methoxy-benzene (3.01 g, [CAS Reg. No. 54788-17-9]) in 1,2-dimethoxyethane (20 mL) was slowly added over a period of 30 minutes. The mixture was stirred for 30 minutes at 0° C. and then for 2 hours at r.t. The reaction mixture was poured into ice and basified with sat. NaHCO3. The aqueous phase was then extracted two times with ethyl acetate and the organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, CH2Cl2) to give the title compound as a light yellow solid (2.45 g, 55%). MS (neg. ion, m/e)=330.3 [(M−H)−].

후처리

  1. additionwas slowly added over a period of 20 minutes
  2. temperatureThe mixture was cooled in an ice bath
  3. waitfor 2 hours at r.t
  4. extractionThe aqueous phase was then extracted two times with ethyl acetate
  5. washthe organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by flash chromatography (silica gel, CH2Cl2)

출처 및 근거

ORD 기록
ord-fd8535a0502047728f147c0bdc29a7ff
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450313B2

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