Methanol → [4-(3-Methoxypropyl)-3-methyl-1-benzofuran-2-yl]methanol

HRID 29470Notes

Reaction equation

HRID 29470 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]2[C:12]([CH3:18])=[C:13]([C:15](O)=[O:16])[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1.[H-].C([Al+]C(C)C)(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]2[C:12]([CH3:18])=[C:13]([CH2:15][OH:16])[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 21896610Diisopropylaluminium hydrideHCID 68710918HCID 68710918, compound

Product 1

HCID 68712813[4-(3-Methoxypropyl)-3-methyl-1-benzofuran-2-yl]methanolYield 96.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4-(3-methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid (0.2354 g, 0.853 mmol) in tetrahydrofuran (10 mL) cooled at 0° C. was added diisopropylaluminium hydride (3.41 mL, of a 1.0M solution in toluene) dropwise. After stirring for 1 hour methanol (5 mL) was added followed by saturated aqueous sodium potassium tartrate (5 mL). The resulting mixture was stirred for 15 minutes and was then thrice extracted with ethyl acetate. Combined organic extracts were dried over sodium sulfate, filtered, reduced to dryness and the resulting residue was subjected to silica gel gradient flash chromatography (hexanes/ ethyl acetate 10:1-3:1) which furnished 0.192 g (96%) of [4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methanol as a white solid. MS (ES) m/z: 234.1 (M+).

Workup

  1. additionwas added
  2. extractionthrice extracted with ethyl acetate
  3. dry with materialCombined organic extracts were dried over sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-991edb97746549968be1f214225c42ad
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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