Methanol → 3-Methyl-2,3-dihydrobenzofuran-4-amine

HRID 230849

Reaction equation

HRID 230849 reaction equation
FC(F)(F)C([NH:5][C:6]1[C:11]2[CH:12]([CH3:15])[CH2:13][O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)=O.O1CCCC1.CO.[OH-].[Li+]>O>[CH3:15][CH:12]1[C:11]2=[C:6]([NH2:5])[CH:7]=[CH:8][CH:9]=[C:10]2[O:14][CH2:13]1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 577632852,2,2-Trifluoro-N-(3-methyl-2,3-dihydro-1-benzofuran-4-yl)acetamide

Product 1

HCID 543264063-Methyl-2,3-dihydrobenzofuran-4-amineYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of Intermediate 24 (0.087 g) in 2:2:1 tetrahydrofuran:methanol:water (5 ml) was added lithium hyroxide (0.149 g) and the mixture stirred at room temperature for 47 h, then at 60° C. for 2.5 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The aqueous layer was re-extracted with dichloromethane and the combined organic layers dried over sodium sulphate and concentrated in vacuo to give the title compound as a colourless oil (0.049 g).

Workup

  1. waitat 60° C. for 2.5 h
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was re-extracted with dichloromethane
  5. dry with materialthe combined organic layers dried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d19e96b5ee8d4e5d9df787ed25d61f4d
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Linked notes

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