Tetrahydrofuran → (6-Phenoxy-benzofuran-2-yl)-methanol

HRID 1171209Notes

Reaction equation

HRID 1171209 reaction equation
O1CCCC1.C([O:8][C:9]([C:11]1[O:12][C:13]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=[CH:16][C:14]=2[CH:15]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[O:20]([C:18]1[CH:17]=[CH:16][C:14]2[CH:15]=[C:11]([CH2:9][OH:8])[O:12][C:13]=2[CH:19]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 576082856-Phenoxy-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 57608210(6-Phenoxy-benzofuran-2-yl)-methanolYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a tetrahydrofuran (5 mL) solution of 6-phenoxy-benzofuran-2-carboxylic acid ethyl ester (251 mg, 889 μmol) described in Production Example 49-1-1 was added lithium aluminum hydride (135 mg, 3.56 mmol) at 0° C., which was stirred at room temperature for 2 hours. To the reaction solution were added water (135 μL), 5 N aqueous sodium hydroxide solution (135 μL) and water (405 μL) at 0° C., followed by filtering through celite. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the title compound (177 mg, 83%) as a colorless oil.

Workup

  1. filtrationby filtering through celite
  2. concentrationThe filtrate was concentrated under a reduced pressure
  3. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-348a89bc7a414dd89ba9aad1c5bc6df7
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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