Water → HCID 49764776, compound

HRID 384991Notes

Reaction equation

HRID 384991 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH:4]([CH:6]1[S:10][CH2:9][CH:8](O)[CH:7]1[N+:12]([O-:14])=[O:13])[CH3:5].S(Cl)(C)(=O)=O.C(N(CC)CC)C.O>ClCCl>[CH3:1][CH:2]([CH3:15])[CH2:3][CH:4]([CH:6]1[C:7]([N+:12]([O-:14])=[O:13])=[CH:8][CH2:9][S:10]1)[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 49764774HCID 49764774, compound

Product 1

HCID 49764776HCID 49764776, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 0.50 g of 5-(4-methylpentan-2-yl)-4-nitrotetrahydrothiophen-3-ol in 4 ml of dichloromethane, 0.27 g of mesyl chloride and 0.33 g of triethylamine were gradually dropped thereto at 4° C. The temperature of the solution was allowed to rise to room temperature, and the solution was stirred for 7.5 hours. Water was added to stop the reaction, and the solution was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and concentrated, and then purified by silica gel chromatography (hexane/ethyl acetate=10/1), thereby obtaining 0.22 g of 2-(4-methylpentan-2-yl)-3-nitro-2,5-dihydrothiophene (yield: 47.7%).

Workup

  1. additionwere gradually dropped
  2. customat 4° C
  3. customto rise to room temperature
  4. customthe reaction
  5. extractionthe solution was extracted with dichloromethane
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-34038c7f05144c2f8313ddc85fb8a00c
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

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