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Trifluoroacetic acid → Methyl 3-((di-tert-butoxyphosphoryloxy)methyl)benzoate

HRID 595036
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 595036
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:13]([O:17][P:18]([O-:25])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:16])([CH3:15])[CH3:14].C([N+](CCCC)(CCCC)CCCC)CCC.O.CO.C(O)(C(F)(F)F)=O>CN(C=O)C.CCOCC>[C:21]([O:20][P:18]([O:25][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])([CH3:24])([CH3:23])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 517981Methyl 3-(bromomethyl)benzoateHCID 22242641Methanol--water (1/1)HCID 22339116Tetra-n-butylammonium di-tert-butylphosphate

Produkt 1

HCID 68385353Methyl 3-((di-tert-butoxyphosphoryloxy)methyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of methyl 3-(bromomethyl)benzoate (1.08 g, 4.71 mmol) in DMF (20 mL) was added tetrabutylammonium di-tert-butyl phosphate (2.34 g, 5.19 mmol). The mixture was stirred at room temperature for 1.5 h, then diluted with ether and washed sequentially with 10% LiCl solution and brine. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The crude material was purified by flash chromatography (Teledyne ISCO CombiFlash 0% to 100% solvent A/B=hexane/EtOAc, REDISEP® SiO2 40 g, detecting at 254 nM, and monitoring at 220 nM). Concentration of appropriate fractions provided Preparation 46A (1.38 g, 82%): HPLC: RT=3.163 min (H2O/MeOH with TFA, CHROMOLITH® ODS, 4.6×50 mm, gradient=4 min, wavelength=220 nm); MS(ES): m/z=359 [M+H+]; 1H NMR (400 MHz, DMSO-d6) δ 8.01 (s, 1H), 7.94-7.89 (m, 1H), 7.66 (d, J=7.9 Hz, 1H), 7.58-7.48 (m, 1H), 5.01 (d, J=8.4 Hz, 2H), 3.86 (s, 3H), 1.41 (s, 18H).

Aufarbeitung

  1. washwashed sequentially with 10% LiCl solution and brine
  2. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography (Teledyne ISCO CombiFlash 0% to 100% solvent A/B=hexane/EtOAc, REDISEP® SiO2 40 g
  6. customConcentration of appropriate fractions provided

Quellen und Nachweise

ORD-Eintrag
ord-0c77a5f264e5447395c4de062696abda
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242941B2

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