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

HRID 1908922Notes

Reaction equation

HRID 1908922 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-e66d3348ef214044985bbc7eeacfecf9
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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