Tetrahydrofuran → 5-(2-Hydroxy-ethyl)-3H-benzoxazol-2-one

HRID 456596Notes

Reaction equation

HRID 456596 reaction equation
N1S[N:4]=[C:3]2[CH:6]=[C:7]([CH2:10][C:11]#N)[CH:8]=[CH:9][C:2]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[OH-:20].[Na+].S([O-])([O-])(=O)=[O:23].[Mg+2].[O:28]1[CH2:32]CCC1>O>[OH:20][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:2]2[O:23][C:32](=[O:28])[NH:4][C:3]=2[CH:6]=1

Participants

8

Reactant 6

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 695224455-Cyanomethylbenz-2,1,3-thiadiazole

Product 1

HCID 179812295-(2-Hydroxy-ethyl)-3H-benzoxazol-2-oneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ester (a) (0.95 g, 4.29 mmol) was added portionwise to a cold solution (0° C.) of lithium aluminium hydride (0.206 g, 4.7 mmol) in tetrahydrofuran (20 ml). The mixture was then stirred 1.5 hours at room temperature and cooled again. The excess of hydride was hydrolysed by careful addition of water (0.2 ml), 5N aqueous sodium hydroxide solution (0.2 ml) and finally water (0.6 ml). Magnesium sulfate was added and the mixture was filtered. The filtrate was concentrated to dryness to give the product (0.5 g, 65%).

Workup

  1. temperaturecooled again
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-b2a5bce6931b4469875ced99a3d86bcb
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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