Methanesulfonyl chloride → HCID 58880523, compound

HRID 2251730Notes

Reaction equation

HRID 2251730 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:16][CH2:15][C:14]3[CH:17]=[C:18]([CH2:21][OH:22])[CH:19]=[CH:20][C:13]=3[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[S:32](Cl)([CH3:35])(=[O:34])=[O:33].C(=O)(O)[O-].[Na+]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[O:16][CH2:15][C:14]3[CH:17]=[C:18]([CH2:21][O:22][S:32]([CH3:35])(=[O:34])=[O:33])[CH:19]=[CH:20][C:13]=3[CH2:12][O:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11536760HCID 11536760, compound

Product 1

HCID 58880523HCID 58880523, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3 g (10 mmol) of [7-(4-nitrophenyl)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl]methanol in 50 ml of dichloromethane are introduced into a flask. 1.54 g (12 mmol) of diisopropylethylamine are added and 1.37 g (12 mmol) of mesyl chloride in solution in 10 ml of dichloromethane are added dropwise at −5° C. After 1 hour 30 minutes of reaction at −5° C., 20 ml of a 5% sodium bicarbonate solution are added, the phases are separated by decantation and the organic phase is washed with water. It is dried over sodium sulfate and the solvent is evaporated off. The crude product is purified by silica gel chromatography (heptane/ethyl acetate: 3/2) to give 0.6 g of methanesulfonic acid [7-(4-nitrophenyl)-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl]methyl ester.

Workup

  1. customAfter 1 hour 30 minutes of reaction at −5° C.
  2. customthe phases are separated by decantation
  3. washthe organic phase is washed with water
  4. dry with materialIt is dried over sodium sulfate
  5. customthe solvent is evaporated off
  6. customThe crude product is purified by silica gel chromatography (heptane/ethyl acetate: 3/2)

Sources & evidence

ORD record
ord-931e0c223c094ea5bc8a05eeb78a8616
Source dataset
uspto-grants-2008_01
Patent number
US07319155B2

Reaction notes

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