Water → HCID 10171308, compound

HRID 1793215Notes

Reaction equation

HRID 1793215 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.[H-].[Al+3].[Li+].[H-].[H-].[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

5

Reactant 3

HCID 962WaterHCID 10236109HCID 10236109, compoundHCID 21226445Aluminium lithium hydride

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 aluminum 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, 300 MHz) 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-85a2f5e267c84706804a0fc80444029f
Source dataset
uspto-grants-2006_07
Patent number
US07078541B2

Reaction notes

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