Tetrahydrofuran → HCID 57608228, compound

HRID 1171203Notes

Reaction equation

HRID 1171203 reaction equation
O1CCCC1.C([O:8][C:9]([C:11]1[O:12][C:13]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[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:17]1[CH:18]=[CH:19][C:13]2[O:12][C:11]([CH2:9][OH:8])=[CH:15][C:14]=2[CH:16]=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 57810562HCID 57810562, compound

Product 1

HCID 57608228HCID 57608228, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a tetrahydrofuran (20 mL) solution of 5-benzyloxy-benzofuran-2-carboxylic acid ethyl ester (890 mg, 3.00 mmol) described in Production Example 7-1-3 was added lithium aluminum hydride (342 mg, 9.00 mmol) at 0° C., which was stirred at room temperature for 3 hours. To the reaction solution were added water (342 μL), 5 N aqueous sodium hydroxide solution (342 μL) and water (1.03 mL) at 0° C. followed by filtering through Celite. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (561 mg, 74%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-d50011af16a64bd4bd5ae648eb95acb4
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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