Methanesulfonyl chloride → HCID 66764789, compound

HRID 402777Notes

Reaction equation

HRID 402777 reaction equation
C([CH:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][CH3:17])[C:12]2[C:7](=[C:8]([O:18][CH3:19])[CH:9]=[CH:10][CH:11]=2)[CH:6]=1)O)C.CS([Cl:24])(=O)=O>C(Cl)Cl>[Cl:24][CH2:3][C:5]1[CH:14]=[C:13]([O:15][CH2:16][CH3:17])[C:12]2[C:7]([CH:6]=1)=[C:8]([O:18][CH3:19])[CH:9]=[CH:10][CH:11]=2

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66764874HCID 66764874, compound

Product 1

HCID 66764789HCID 66764789, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl (4-ethoxy-8-methoxynaphthalen-2-yl)methanol (0.136 g, 0.59 mmol) and TEA (0.25 mL, 1.76 mmol) in dry CH2Cl2 (6 mL) was added MsCl (0.068 mL, 0.88 mmol). The resulting reaction mixture was stirred at room temperature overnight and was then diluted with CH2Cl2 (25 mL) and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified on a silica gel column eluting with a gradient of 100% hexanes to 10% EtOAc/hexanes to give the title intermediate (23 mg) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column
  7. washeluting with a gradient of 100% hexanes to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-dd8067649c1b4f7aab4a1cda47f79962
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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