Sodium Hydroxide → ((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

HRID 2407259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407259
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C(=O)C)=[C:11]([O:19][CH2:20][C@H:21]2[CH2:23][O:22]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][C@@H:21]([CH2:23][OH:22])[CH2:20][O:19][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86644714Acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

Produkt 1

HCID 66726995((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester (1.34 g, 4.26 mmol) in THF (30 ml), was added aq 2 M NaOH (2.45 ml). The mixture was stirred overnight at RT, THF was removed under reduced pressure and water (50 ml) was added. The water solution was then extracted three times with EtOAc and the combined extracts washed with water and brine. The organic layer was dried (Na2SO4), and evaporated in vacuo. The crude product (1.07 g) was used without purification.

Aufarbeitung

  1. customTHF was removed under reduced pressure and water (50 ml)
  2. additionwas added
  3. extractionThe water solution was then extracted three times with EtOAc
  4. washthe combined extracts washed with water and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe crude product (1.07 g) was used without purification

Quellen und Nachweise

ORD-Eintrag
ord-67e549dcef684219998390087040ccac
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809536B2

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