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

HRID 15679Notes

Reaction equation

HRID 15679 reaction equation
[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>[CH3:15][O:11][C:10](=[O:12])[CH2:9][C@H:6]1[C:5]2[CH:13]=[CH:14][C:2]([OH:1])=[CH:3][C:4]=2[O:8][CH2:7]1

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

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.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-d7feccbbbb364cd2b29ad19b7d46332a
Source dataset
uspto-grants-2010_06
Patent number
US07732626B2

Reaction notes

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