Isopropyl iodide → 2-Hydroxymethyl-4-isopropoxy-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

HRID 1177211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177211
I[CH:2]([CH3:4])[CH3:3].[C:5]([O:9][C:10]([C:12]1[CH:22]=[C:21]([OH:23])[C:15]2[CH2:16][CH:17]([CH2:19][OH:20])[O:18][C:14]=2[CH:13]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:5]([O:9][C:10]([C:12]1[CH:22]=[C:21]([O:23][CH:2]([CH3:4])[CH3:3])[C:15]2[CH2:16][CH:17]([CH2:19][OH:20])[O:18][C:14]=2[CH:13]=1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Komponenten

5

Edukt 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium Carbonate2×HCID 25067321tert-Butyl 4-hydroxy-2-(hydroxymethyl)-2,3-dihydrobenzofuran-6-carboxylate

Produkt 1

HCID 595601892-Hydroxymethyl-4-isopropoxy-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl esterAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-iodopropane (0.826 mL, 8.26 mmol), 4-hydroxy-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (200f) (2.00 g, 7.51 mmol), and K2CO3 (1.56 g, 11.3 mmol) in DMF (20 mL) was heated to 60° C. overnight. Additional 2-iodopropane (0.9 mL) and K2CO3 (0.9 g) were added. The resulting mixture was heated to 50° C. for 4 days, then cooled to room temperature, quenched with H2O and extracted with 3×EtOAc. The organic layers were washed with 2× H2O, dried over Na2SO4, and concentrated. The residue was purified by flash column chromatography with 50-70% EtOAc in hexanes to give a yellow syrup (2.0 g, 86% yield). 1H NMR (400 MHz, CDCl3) δ 7.11 (s, 1 H) 7.03 (d, J=1.01 Hz, 1 H) 4.90-5.05 (m, 1 H) 4.58-4.66 (m, 1 H) 3.81-3.88 (m, 1 H) 3.67-3.77 (m, 1 H) 3.21 (dd, J=16.42, 9.60 Hz, 1 H) 2.94 (dd, J=16.42, 7.07 Hz, 1 H) 1.60 (s, 9 H) 1.32-1.34 (m, 6 H); LCMS for C17H24O5 m/z 253.00 (M-tBu+H+).

Aufarbeitung

  1. temperatureThe resulting mixture was heated to 50° C. for 4 days
  2. temperaturecooled to room temperature
  3. customquenched with H2O
  4. extractionextracted with 3×EtOAc
  5. washThe organic layers were washed with 2× H2O
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography with 50-70% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-69f8ceae80304fd38d8c199750563cba
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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