Methanesulfonyl chloride → 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate

HRID 1719804Notes

Reaction equation

HRID 1719804 reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)[CH:4]([OH:6])[CH3:5].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[CH3:21][S:22]([O:6][CH:4]([CH3:5])[C:3]([O:19][CH3:20])([O:2][CH3:1])[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 113003471,1-Dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol

Product 1

HCID 127563301,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.2 G of 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol is dissolved in 10 ml of pyridine and 1.1 g of methanesulfonyl chloride is added to that solution in one portion. The mixture is allowed to stand for about three hours and the separation of pyridine hydrochloride crystals is observed. The reaction mixture is poured into 100 ml of water and extracted with 50 ml of ether. The ethereal extract is washed several times with water and dried over magnesium sulfate. The ethereal layer is evaporated under reduced pressure to afford 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate as an oil. The compound displays a characteristic NMR spectra in the deuterochloroform of τ=9.0 (doublet, J=2), 6.85, 6.70, 6.61, 6.07, 4.89 (quartet, J=2), 1.99-2.88 (multiplet).

Workup

  1. customthe separation of pyridine hydrochloride crystals
  2. additionThe reaction mixture is poured into 100 ml of water
  3. extractionextracted with 50 ml of ether
  4. extractionThe ethereal extract
  5. washis washed several times with water
  6. dry with materialdried over magnesium sulfate
  7. customThe ethereal layer is evaporated under reduced pressure

Sources & evidence

ORD record
ord-4f2275a943ae459690bd6d4bcaca6124
Source dataset
uspto-grants-1985_09
Patent number
US04542237

Reaction notes

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