Sodium borohydride → Ethyl 2-(hydroxymethyl)-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate

HRID 1177286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177286
[CH:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]([O:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[C:6]=2[CH:7]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]([O:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[C:6]=2[CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 86624767Ethyl 2-formyl-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate

Produkt 1

HCID 66755904Ethyl 2-(hydroxymethyl)-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-formyl-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate (285b) (230 mg, 0.592 mmol) in MeOH (10 mL) was added NaBH4 (50 mg, 1.3 mmol). The mixture was stirred for half an hour. The solvent was evaporated, and the product was purified by gradient silica gel chromatography using CHCl3/MeOH (100/0 to 98/2). The desired compound was isolated as a white solid (170 mg, 74%). 1 H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.40 (t, J=7.16 Hz, 3 H) 1.99 (t, J=6.22 Hz, 1 H) 3.06 (s, 3 H) 4.39 (q, J=7.16 Hz, 2 H) 4.78 (d, J=6.22 Hz, 2 H) 6.52 (d, J=1.13 Hz, 1 H) 7.00-7.17 (m, 2 H) 7.64 (d, J=1.13 Hz, 1 H) 7.87-7.97 (m, 2 H) 8.06 (s, 1 H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe product was purified by gradient silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3f770fa649574ddca2d1fdf43907ffb1
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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