Potassium Carbonate → 4-tert-Butyl-3-(3-methoxy-propoxy)-benzoic acid methyl ester

HRID 1158465노트

반응식

HRID 1158465 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[C:6]([OH:14])[CH:5]=1.[CH3:16][O:17][CH2:18][CH2:19][CH2:20]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:11])([CH3:12])[CH3:13])=[C:6]([O:14][CH2:20][CH2:19][CH2:18][O:17][CH3:16])[CH:5]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 233453414-tert-Butyl-3-hydroxy-benzoic acid methyl ester

생성물 1

HCID 686413504-tert-Butyl-3-(3-methoxy-propoxy)-benzoic acid methyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 4-tert-butyl-3-hydroxy-benzoic acid methyl ester (1.56 g, 7.49 mmol), 3-bromopropyl methyl ether (1.72 g, 11.2 mmol) and anhydrous K2CO3 (1.55 g, 11.2 mmol) in MeCN (30 mL) is refluxed overnight. After cooling, the mixture is filtered, the filtrate is diluted with CH2Cl2 and the organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 97:3) gives the title compound as colorless oil. MS: 281.1 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 6.22 min. 1H-NMR (CDCl3): δ 1.43 (s, 9H), 2.17 (m, 2H), 3.41 (s, 3H), 3.65 (m, 2H), 3.93 (s, 3H), 4.18 (m, 2H), 7.36 (dd, 1H), 7.96 (d, 1H), 7.60 (dd, 1H) ppm.

후처리

  1. temperatureis refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. additionthe filtrate is diluted with CH2Cl2
  5. washthe organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by flash chromatography on silica gel (hexane/AcOEt 97:3)

출처 및 근거

ORD 기록
ord-f9d629d8847d4122866a7fbda4c65350
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807709B2

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