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

HRID 453470노트

반응식

HRID 453470 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

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.

후처리

  1. additionwas added

출처 및 근거

ORD 기록
ord-8ad68d803ebc48f188c13d3f238971b0
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492430B2

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