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

HRID 1171188Notes

Reaction equation

HRID 1171188 reaction equation
O1CCCC1.C([O:8][C:9]([C:11]1[O:12][C:13]2[CH:19]=[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]=[CH:16][C:14]=2[CH:15]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH2:21]([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:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57810532Ethyl 6-(Benzyloxy)benzofuran-2-carboxylate

Product 1

HCID 57608261(6-Benzyloxy-benzofuran-2-yl)-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a tetrahydrofuran (370 mL) solution of 6-benzyloxy-benzofuran-2-carboxylic acid ethyl ester (18.4 g, 62.1 mmol) described in Production Example 1-2-1 was added lithium aluminum hydride (7.07 g, 186 mmol) at 0° C., which was stirred at room temperature for 4 hours. To the reaction mixture were added water (7.07 mL), 5 N aqueous sodium hydroxide solution (7.07 mL) and water (21.2 mL) at 0° C. After filtering the mixture through Celite, the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (14.2 g, 90%) as a white solid.

Workup

  1. filtrationAfter filtering the mixture through Celite
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f80340ace6ac4dfdad89798309d9f373
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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