Borane;tetrahydrofuran → 5-(2-hydroxy-1-methylethyl)-4-methyl-2-benzofuran-1(3H)-one

HRID 2173173Notes

Reaction equation

HRID 2173173 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]([CH3:16])[C:13](O)=[O:14].B.C1COCC1>C1COCC1>[OH:14][CH2:13][CH:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[CH3:1])[CH3:16]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 675132282-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propanoic acid

Product 1

HCID 666438615-(2-hydroxy-1-methylethyl)-4-methyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propanoic acid (300 mg, 1.4 mmol) in 18 mL of anhydrous THF was added BH3.THF (2 mL, 2 mmol) dropwise at 0° C. Then the mixture was warmed to room temperature slowly and then stirred for 3 hours. Then the mixture was quenched with MeOH and the solvent was removed under vacuum. The residue was the purified via prep-TLC to give 5-(2-hydroxy-1-methylethyl)-4-methyl-2-benzofuran-1(3H)-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.73 (d, J=7.8 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 5.23 (s, 2H), 3.77 (d, J=7.0 Hz, 2H), 3.36˜3.42 (m, 1H), 2.30 (s, 3H), 1.27 (d, J=7.0 Hz, 3H).

Workup

  1. customThen the mixture was quenched with MeOH
  2. customthe solvent was removed under vacuum
  3. custompurified via prep-TLC

Sources & evidence

ORD record
ord-c9bbf77df94749b8964befc4423ceba3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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