Water → HCID 49764775, compound

HRID 384990Notes

Reaction equation

HRID 384990 reaction equation
[N+:1]([CH:4]1[CH:8]([CH:9]([CH2:11][CH2:12][CH3:13])[CH3:10])[S:7][CH2:6][CH:5]1O)([O-:3])=[O:2].S(Cl)(C)(=O)=O.C(N(CC)CC)C.O>ClCCl>[N+:1]([C:4]1[CH:8]([CH:9]([CH2:11][CH2:12][CH3:13])[CH3:10])[S:7][CH2:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 49764773HCID 49764773, compound

Product 1

HCID 49764775HCID 49764775, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 150 mg of 4-nitro-5-(pentan-2-yl)tetrahydrothiophen-3-ol in 4 ml of dichloromethane, 86 mg of mesyl chloride and 138 mg 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 3.5 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 78 mg of 3-nitro-2-(pentan-2-yl)-2,5-dihydrothiophene (yield: 57.3%).

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-e6c2261f79bc42f2ab92be8b0a8247fd
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

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