Dichloromethane → 5-(Chloromethyl)-6-methyl-1,3-dihydro-2-benzofuran

HRID 2047262Notes

Reaction equation

HRID 2047262 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[C:10]([CH2:18]O)=[CH:11][C:12]2[CH2:16][O:15][CH2:14][C:13]=2[CH:17]=1.[Cl:20]CCl.CS(Cl)(=O)=O>O>[Cl:20][CH2:18][C:10]1[C:9]([CH3:8])=[CH:17][C:13]2[CH2:14][O:15][CH2:16][C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86691253(6-Methyl-1,3-dihydroisobenzofuran-5-yl)methanol

Product 1

HCID 866912545-(Chloromethyl)-6-methyl-1,3-dihydro-2-benzofuranYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (1.7 mL, 12 mmol) was added under ice cooling to a mixture of (6-methyl-1,3-dihydro-2-benzofuran-5-yl)methanol described in Production Example 1-5 (1.0 g, 6.1 mmol) and dichloromethane (10 mL), followed by the addition of methanesulfonyl chloride (470 μL, 6.1 mmol) at that temperature. The reaction mixture was stirred for 3 hours at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:10) to give the title compound (680 mg, 61% yield).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:10)

Sources & evidence

ORD record
ord-6777390e3741446d958c40dbaa3c83c3
Source dataset
uspto-grants-2013_11
Patent number
US08592470B2

Reaction notes

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