Triethylamine → 5-(Chloromethyl)-2,3-dihydro-1-benzofuran

HRID 7423

Reaction equation

HRID 7423 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([CH2:10]O)[CH:8]=[CH:9][C:2]1=2.C(N(CC)CC)C.CS([Cl:23])(=O)=O>ClCCl>[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([CH2:10][Cl:23])[CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2776158(2,3-Dihydro-1-benzofuran-5-yl)methanol

Product 1

HCID 117896145-(Chloromethyl)-2,3-dihydro-1-benzofuranYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,3-dihydrobenzo[b]furan-5-yl)methanol (1.5 g, 10 mmol) in dichloromethane (10 mL) were added under ice-cooling triethylamine (1.67 mL, 12 mmol) and methanesulfonyl chloride (0.85 mL, 10 mmol) and the mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1.6 g, 100%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-481ec1a85eb24912b47c7efbb63a5f15
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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