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

HRID 1158465ノート

反応式

HRID 1158465 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f9d629d8847d4122866a7fbda4c65350
出典データセット
uspto-grants-2010_10
特許番号
US07807709B2

反応ノート

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