Reaktion #43957

Reaktionsgleichung

hydrogen

(6-hydroxy-1-benzofuran-3-yl)acetate

sodium methoxide

→

Methyl[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate

Lösungsmittel

methanol

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added

Vorschrift

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.

Quelle