2-(6-Methoxy-1-benzofuran-3-yl)acetic acid → 2-(6-Methoxy-2,3-dihydro-1-benzofuran-3-yl)acetic acid

HRID 15677Notes

Reaction equation

HRID 15677 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:8][O:9][C:5]=2[CH:4]=1.C[O-].[Na+].[H][H]>CO>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[CH:7]([CH2:10][C:11]([OH:13])=[O:12])[CH2:8][O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 7368182-(6-Methoxy-1-benzofuran-3-yl)acetic acidHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 570770112-(6-Methoxy-2,3-dihydro-1-benzofuran-3-yl)acetic acidYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (1,5-cyclooctadiene)rhodium trifluoromethanesulfonate (5.9 mg) and (S,S)-Et-FerroTANE (5.5 mg) was added methanol (2.5 mL) sufficiently substituted by argon gas, and the mixture was stirred at room temperature for 15 min. This was added to a mixture of (6-methoxy-1-benzofuran-3-yl)acetic acid (51.5 mg) and sodium methoxide (7 mg), and the mixture was stirred at room temperature for 5 hr under 0.7 MPa hydrogen atmosphere. The reaction mixture was quantified by HPLC. As a result, the enantiomeric excess was 86.2%, and the yield was 88.4%.

Sources & evidence

ORD record
ord-6e667e7307d94b30b1ee0ffbad30c7bd
Source dataset
uspto-grants-2010_06
Patent number
US07732626B2

Reaction notes

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