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

HRID 15678Notes

Reaction equation

HRID 15678 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([C:9](O)=O)=[CH:7][O:8][C:4]=2[CH:3]=1.[CH3:14][O-:15].[Na+].[H][H].C[OH:20]>>[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[CH:6]([CH2:9][C:14]([OH:20])=[O:15])[CH2:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 887Methanol3×HCID 10942334Sodium MethoxideHCID 13940753HCID 13940753, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23111800(6-Hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetic acidYield 98.5%

Procedure

To a mixture of (1,5-cyclooctadiene)rhodium trifluoromethanesulfonate (47 mg) and (S,S)-Et-FerroTANE (44 mg) was added methanol (15 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)carboxylic acid (1.92 g) and sodium methoxide (270 mg) was added methanol (35 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 91.2%, and the yield was 98.5%.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-ea3400e2811c4359a54ee502e3cbf737
Source dataset
uspto-grants-2010_06
Patent number
US07732626B2

Reaction notes

Loading…