2-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propanoic acid → 5-(2-hydroxy-1-methylethyl)-4-methyl-2-benzofuran-1(3H)-one

HRID 1186960Notes

Reaction equation

HRID 1186960 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]>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

3

Reactant 1

HCID 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 8028TetrahydrofuranSolvent2×

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.

Workup

  1. customdropwise at 0° C
  2. customThen the mixture was quenched with MeOH
  3. customthe solvent was removed under vacuum
  4. custompurified via prep-TLC

Sources & evidence

ORD record
ord-49aeab46a5634d88bbfbd1157a250e58
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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