Water → HCID 10171308, compound

HRID 480986Notes

Reaction equation

HRID 480986 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]2[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([OH:16])=[CH:10][C:8]=2[CH:9]=1)=O.[Li].[H-].O>C1COCC1>[OH:2][CH2:3][C:5]1[O:6][C:7]2[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([OH:16])=[CH:10][C:8]=2[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 3028194LithiumHCID 10236109HCID 10236109, compound

Product 1

HCID 10171308HCID 10171308, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid methyl ester (231 mg) prepared as in Example 2, was dissolved in THF and lithium alumininum hydride (93 mg) was added. The mixture was stirred at room temperature for 4 h. Then the solution was poured into water and extracted with ethylacetate. The ethyl acetate was washed with water and brine, dried over MgSO4 and concentrated. Purification by silica gel column eluting with 50% EtOAc in hexane gave 89 mg of 2-Hydroxymethyl-6,7-dimethyl-benzofuran-5-ol. 1HNMR (CD3OD, 300MHz) δ: 6.75, 1H), 6.47 (s, 1H), 4.61 (s, 2H), 2.37 (s, 3H), 2.20 (s, 3H) ppm. 13CNMR (CD3OD, 75 MHz) δ: 155.87, 150.51, 148.68, 124.69, 119.93, 119.20, 103.01, 101.62, 56.32, 10.43, 10.29 ppm. MS: 175 (M—OH)+.

Workup

  1. extractionextracted with ethylacetate
  2. washThe ethyl acetate was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by silica gel column
  6. washeluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-e26c562eda4a46d78c3be5c3df738a2c
Source dataset
uspto-grants-2003_11
Patent number
US06653346B1

Reaction notes

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