(6-Hydroxy-1-benzofuran-3-yl)acetate → (S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

HRID 1908923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908923
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([O-:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.[CH3:15][O-].[Na+].[H][H]>CO>[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C@H:6]([CH2:9][C:10]([O:12][CH3:15])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 2110914(6-Hydroxy-1-benzofuran-3-yl)acetateHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Versuchsvorschrift

To a mixture of (1,5-cyclooctadiene)rhodium trifluoromethanesulfonate (656 mg) and (S,S)-Et-FerroTANE (620 mg) was added methanol (200 mL) sufficiently substituted by argon gas, and the mixture was stirred at room temperature 15 min. To a mixture of (6-hydroxy-1-benzofuran-3-yl)acetate (26.1 g) and sodium methoxide (3.8 g) was added methanol (500 mL) sufficiently substituted by argon gas. The methanol solution prepared earlier was added thereto, and the mixture was stirred at room temperature for 2 hr under 0.7 MPa hydrogen atmosphere. The reaction mixture was quantified by HPLC. As a result, the enantiomeric excess was 90.8%, the yield was quantitative.

Aufarbeitung

  1. additionwas added

Quellen und Nachweise

ORD-Eintrag
ord-89a3589a6b5b4abf846c8f14b84ad239
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598226B2

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