Tetrahydrofuran → HCID 53486849, compound

HRID 1477606Notes

Reaction equation

HRID 1477606 reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([C:15](O)=[O:16])=[CH:12][C:11]=2[CH:18]=1.B.O1CCCC1>CO>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([CH2:15][OH:16])=[CH:12][C:11]=2[CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 9378385-Chloro-1-benzofuran-2-carboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 53486849HCID 53486849, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a tetrahydrofuran solution (12 mL) of 5-chlorobenzofuran-2-carboxylic acid (620 mg, 3.15 mmol), borane-tetrahydrofuran complex (7.88 mL, 7.88 mmol, tetrahydrofuran solution) was added at 0° C. and the resultant solution was stirred at room temperature for 3 hours, at 60° C. for 1 day, and at room temperature for 1 day. After completion of the reaction, concentration under reduced pressure was carried out three times with adding methanol to the reaction solution and the concentrated solution was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1 (v/v)) to obtain the title compound (268 mg, yield 47%).

Workup

  1. customAfter completion of the reaction, concentration under reduced pressure
  2. customthe concentrated solution was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→1/1 (v/v))

Sources & evidence

ORD record
ord-a6abf6ceb701419f80b1592ede994934
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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