Pyridine → HCID 178487221, compound

HRID 2165149Notes

Reaction equation

HRID 2165149 reaction equation
N1C=CC=CC=1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[CH:20]=[C:19]([CH2:21][OH:22])[C:18]=2[CH:23]=1>ClCCl>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[CH:20]=[C:19]([CH2:21][O:22][S:8]([CH3:7])(=[O:10])=[O:9])[C:18]=2[CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 23044250HCID 23044250, compound

Product 1

HCID 178487221HCID 178487221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.1 ml (76 mmol) of pyridine and 3.6 ml (46 mmol) of methanesulphonic acid chloride are added at 0° C., while stirring, with the exclusion of moisture, to 5.0 g (30.5 mmol) of (5-methoxybenzocyclobuten-1-yl)methanol in 50 ml of dichloromethane. The mixture is then stirred at room temperature for a further 18 hours to complete the reaction. 50 ml of ice-water are then added and the whole is stirred for 30 minutes. The organic phase is separated off, washed once in each case with 2N sodium hydroxide solution, 2N hydrochloric acid and water, dried over sodium sulphate and concentrated under reduced pressure. Methanesulphonic acid (5-methoxybenzocyclobuten-1-ylmethyl) ester is obtained in the form of a viscous oil, Rf=0.4, toluene/ethyl acetate (9:1).

Workup

  1. customthe reaction
  2. stirringthe whole is stirred for 30 minutes
  3. customThe organic phase is separated off
  4. washwashed once in each case with 2N sodium hydroxide solution, 2N hydrochloric acid and water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69970ee26a5d4be0bf1a2fce2bdb40d8
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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