Tetrahydrofuran → HCID 66921872, Verbindung

HRID 1364014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364014
[Br:1][C:2]1[C@@H:7](O)[C@@H:6]([OH:9])[C@@H:5]([NH:10][C:11](=[O:13])[CH3:12])[C@H:4]([O:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:3]=1.C(OC(C)(C)C([Br:27])=O)(=O)C.C1C[O:33][CH2:32][CH2:31]1>>[C:32]([O:9][C@H:6]1[C@@H:5]([NH:10][C:11](=[O:13])[CH3:12])[C@H:4]([O:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:3]=[C:2]([Br:1])[C@@H:7]1[Br:27])(=[O:33])[CH3:31]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 27247151-Bromocarbonyl-1-methylethyl acetateHCID 25019473HCID 25019473, Verbindung

Produkt 1

HCID 66921872HCID 66921872, Verbindung

Versuchsvorschrift

To a stirred solution of diol 23 (7.42 g, 22.1 mmol) in THF (150 mL) at 0° C. under nitrogen atmosphere, α-acetoxyisobutyryl bromide (4.1 mL, 27.8 mmol) was added dropwise over a period of 10 min. The reaction mixture was stirred at same temperature for 30 min, and warmed to room temperature with stirring for 3.5 h. The solvent was evaporated, and the residual oil was partitioned between EtOAc (200 mL) and 5% aqueous NaHCO3 (50 mL). The organic layer was washed with water (100 mL), dried over MgSO4, filtered and concentrated to afford the crude bromoacetate 24 (9.05 g). The crude product was used in the next step without further purification.

Aufarbeitung

  1. stirringwith stirring for 3.5 h
  2. customThe solvent was evaporated
  3. customthe residual oil was partitioned between EtOAc (200 mL) and 5% aqueous NaHCO3 (50 mL)
  4. washThe organic layer was washed with water (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e2e8382a46104cf7afb321f156115f6d
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888337B2

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