2-(6-Hydroxy-1-benzofuran-3-yl)acetic acid → HCID 60164157, compound

HRID 1848793Notes

Reaction equation

HRID 1848793 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.C[O-].[Na+]>>[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C@H:6]([CH2:9][C:10]([OH:12])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 21109152-(6-Hydroxy-1-benzofuran-3-yl)acetic acidHCID 10942334Sodium Methoxide

Product 1

HCID 60164157HCID 60164157, compoundYield 99.9%

Procedure

(6-Hydroxy-1-benzofuran-3-yl)acetic acid (0.050 g, 0.26 mmol) and dichloro[(+)-1,2-bis((2R,5R)-2,5-diisopropylphosphorano)benzene]ruthenium (II)-N,N-dimethylformamide complex (1.9 mg, 0.0026 mmol) and sodium methoxide (14.0 mg, 0.26 mmol) were charged, and purged with argon. Methanol (1 mL) was added thereto, and the mixture was stirred at room temperature for 12 hr under a hydrogen atmosphere (1.0 MPa). The obtained reaction mixture was analyzed by liquid chromatography to give the title compound (conversion ratio 99.9%, optical purity 84.1% ee(S)).

Workup

  1. custompurged with argon
  2. additionMethanol (1 mL) was added
  3. customThe obtained reaction mixture

Sources & evidence

ORD record
ord-f6e02682e53c4331938c8e07dbfc2810
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

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