Hydrogen Peroxide → [(S)-6-((R)-7-Fluoro-4-hydroxyindan-1-yloxy)-2,3-dihydrobenzofuran-3-yl]-acetic acid methyl ester

HRID 2408528Notes

Reaction equation

HRID 2408528 reaction equation
[OH:1]O.[CH3:3][O:4][C:5](=[O:36])[CH2:6][C@H:7]1[C:11]2[CH:12]=[CH:13][C:14]([O:16][C@H:17]3[C:25]4[C:20](=[C:21](B5OC(C)(C)C(C)(C)O5)[CH:22]=[CH:23][C:24]=4[F:26])[CH2:19][CH2:18]3)=[CH:15][C:10]=2[O:9][CH2:8]1.[OH-].[Na+]>C(O)(=O)C>[CH3:3][O:4][C:5](=[O:36])[CH2:6][C@H:7]1[C:11]2[CH:12]=[CH:13][C:14]([O:16][C@H:17]3[C:25]4[C:20](=[C:21]([OH:1])[CH:22]=[CH:23][C:24]=4[F:26])[CH2:19][CH2:18]3)=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86697106{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 86720104[(S)-6-((R)-7-Fluoro-4-hydroxyindan-1-yloxy)-2,3-dihydrobenzofuran-3-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Aqueous hydrogen peroxide solution (35%, 3.7 mL) is added dropwise to a solution of {(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (5.0 g) in acetic acid (30 mL) chilled in an ice bath. The solution is stirred with cooling for 0.5 h and at room temperature for another 2 h. Ice-cold water (50 mL) and 2 N aqueous NaOH solution (20 mL) are added, and the mixture is stirred at room temperature overnight. The mixture is extracted with ethyl acetate, and the combined extracts are washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40) to give the title compound. LC (method 2): tR=1.01 min; Mass spectrum (ESI+): m/z=359 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. stirringthe mixture is stirred at room temperature overnight
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe combined extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40)

Sources & evidence

ORD record
ord-7f3acc0443ba49a68563d5297b394c0f
Source dataset
uspto-grants-2014_08
Patent number
US08815864B2

Reaction notes

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