Water → Methyl 4-([1,1'-biphenyl]-3-ylmethoxy)benzenepropanoate

HRID 1678567

반응식

HRID 1678567 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.B([O-])O[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C(CO)=CC=CC=1.O>[C:2]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoateHCID 178514829HCID 178514829, 화합물

생성물 1

HCID 23082944Methyl 4-([1,1'-biphenyl]-3-ylmethoxy)benzenepropanoate수율 93.4%

시약·촉매·용매 1

HCID 66808090HCID 66808090, 화합물용매

실험 절차

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (0.60 g, 1.7 mmol), phenyl boronate (0.25 g, 2.1 mmol) and sodium carbonate (0.55 g, 5.2 mmol) were dissolved in toluene-methanol-water (5:1:1, 35 mL), the mixture was purged with argon, and then tetrakistriphenylphosphine palladium (99 mg, 0.086 mmol) was added thereto. The reaction solution was heated under reflux overnight under argon atmosphere. The reaction solution was cooled, and then water was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with water, dried and then concentrated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.55 g, yield 92%) as white powders.

후처리

  1. customthe mixture was purged with argon
  2. temperatureThe reaction solution was heated
  3. temperatureunder reflux overnight under argon atmosphere
  4. temperatureThe reaction solution was cooled
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1)

출처 및 근거

ORD 기록
ord-0b4f74c77ac3488fa3fa43aa98fc548c
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008525B2

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