Ethyl Acetate → N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide

HRID 594381

Reaktionsgleichung

Reaktionsgleichung von HRID 594381
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=O.[CH3:16][C:17]([S:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[N:22][S:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 220843Dibenzo(b,d)furan-2-carboxaldehydeHCID 3382465Tert-Butanesulfinamide

Produkt 1

HCID 86695630N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of commercially available dibenzo[b,d]furan-2-carbaldehyde (1.992 g; 10.20 mmol), titanium(IV) ethoxide Ti(OEt)4 (3.98 ml; 19.00 mmol), and 2-methylpropane-2-sulfinamide (1.150 g; 9.49 mmol) in anh. THF (18 ml) was stirred at rt, under nitrogen, for 4 h. AcOEt and brine were added, and the organic layer was further washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM) afforded N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide as a pale yellow solid. LC-MS (conditions A): tR=0.96 min.; [M+H]+: 300.33 g/mol.

Aufarbeitung

  1. washthe organic layer was further washed with brine
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by FC (DCM)

Quellen und Nachweise

ORD-Eintrag
ord-52acc40b5af041ff86e04ebb99c8d6e1
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242970B2

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