N-Fluorobenzenesulfonimide → HCID 57900344, compound

HRID 84716Notes

Reaction equation

HRID 84716 reaction equation
[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[O:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:14]([OH:16])=[O:15].C([Li])(C)(C)C.[F:22]N(S(C1C=CC=CC=1)(=O)=O)S(C1C=CC=CC=1)(=O)=O>C1COCC1.CCCCC>[F:22][C:3]1[C:4]2[CH2:5][O:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[S:1][C:2]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 21138884H-thieno[3,2-c]chromene-2-carboxylic acidHCID 178418306HCID 178418306, compound

Product 1

HCID 57900344HCID 57900344, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To 4H-thieno[3,2-c]chromene-2-carboxylic acid (1.65 g, 7.10 mmol) in THF (70 mL) at −78° C. was added a 1.5 M solution of tert-butyllithium in pentane (15 mL). The resulting solution stirred 1 hr at −78° C. N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (7.2 g, 23 mmol) was added and the reaction warmed to room temperature over 2 hr. The reaction was quenched by the addition of 1 M HCl to effect pH 3. The aqueous layer was extracted with CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo to yield 3-fluoro-4H-thieno[3,2-c]chromene-2-carboxylic acid, which contained less than 40% 4H-thieno[3,2-c]chromene-2-carboxylic acid, which was utilized in the next step without purification (1.0 g). MS (Q1) 249 (M)+

Workup

  1. temperaturethe reaction warmed to room temperature over 2 hr
  2. customThe reaction was quenched by the addition of 1 M HCl
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cff264d34284626ad612e04830bf154
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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