Tetrahydrofuran → 2,3-Dihydro-3-(2-hydroxyethyl)benzo[b]furan

HRID 963211Notes

Reaction equation

HRID 963211 reaction equation
C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:12]1[CH2:16][CH:15]([CH2:17][C:18](OCC)=[O:19])[C:14]2[CH:23]=[CH:24][CH:25]=[CH:26][C:13]1=2.[OH-].[Na+]>O>[OH:19][CH2:18][CH2:17][CH:15]1[CH2:16][O:12][C:13]2[CH:26]=[CH:25][CH:24]=[CH:23][C:14]1=2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12171952Ethyl 2,3-dihydrobenzo[1,2-b]furan-3-acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 113211472,3-Dihydro-3-(2-hydroxyethyl)benzo[b]furanYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
22 °C

Procedure

To a stirred 0° C. solution of THF (~50 mL) containing LAH (0.86 g, 22.6 mmol) under N2 atmosphere was added dropwise a THF solution of ethyl 2,3-dihydrobenzo[1,2-b]furan-3-acetate (2.50 g, 11.3 mmol). After complete addition the reaction was allowed to warm to 22° C. and stand for two h. The reaction was cooled to 0° C. and treated sequentially with water (0.9 mL), 15% NaOH (0.9 mL), and water (2.7 mL). After stirring for 2 h the reaction was filtered through Celite and the filter cake washed with THF and Et2O. The organic filtrate was dried with anhydrous MgSO4, filtered, and concentrated in vacuo to afford a the title compound (1.85 g, >99%) as a yellow oil which was used without further purification.

Workup

  1. additionAfter complete addition the reaction
  2. temperatureThe reaction was cooled to 0° C.
  3. filtrationwas filtered through Celite
  4. washthe filter cake washed with THF and Et2O
  5. dry with materialThe organic filtrate was dried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77b058ddbb60456a8dce5bf6b60e8232
Source dataset
uspto-grants-1998_06
Patent number
US05763444

Reaction notes

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