Water → HCID 58668701, compound

HRID 2356973Notes

Reaction equation

HRID 2356973 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=O)[CH2:15][CH2:16][O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21](P(=O)(OCC)OCC)#[N:22].[C-]#N.[Li+].O>O1CCCC1>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]([C:21]#[N:22])[CH2:15][CH2:16][O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 75478Lithium cyanideHCID 76257Diethyl cyanophosphonateHCID 57675682HCID 57675682, compound

Product 1

HCID 58668701HCID 58668701, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Benzenesulfonyl-chroman-4-one from Preparation 1 above (500 mg, 1.73 mmol) was dissolved in 10 mL of tetrahydrofuran (THF). Diethyl cyanophosphonate (789 uL, 5.21 mmol) and lithium cyanide (10.42 mL, 5.21 mmol) were added, and the reaction mixture was stirred for 10 minutes at room temperature. Water (150 (mL) was added, and the aqueous mixture was extracted twice with 200 mL of EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure. The residue was dissolved in 5 mL THF, and 70 mL of MeOH was added. SmI2 (52 mL, 5.21 mmol) was then added over five minutes, and the reaction mixture was stirred for 10 minutes at room temperature. The reaction was quenched by addition of 20 mL 1 N HCl, and the resulting aqueous mixture was extracted with EtOAc and 1 N Na2S2O3. The organic phase was dried over MgSO4, and solvent was removed under reduced pressure. The residue eluted through silica gel using 40% EtOAc in hexanes, and solvent was removed under reduced pressure to yield 300 mg (1 mmol, 58%) of 7-benzenesulfonyl-chroman-4-carbonitrile. MS: 300 (M+H)+.

Workup

  1. extractionthe aqueous mixture was extracted twice with 200 mL of EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 5 mL THF
  6. addition70 mL of MeOH was added
  7. stirringthe reaction mixture was stirred for 10 minutes at room temperature
  8. customThe reaction was quenched by addition of 20 mL 1 N HCl
  9. extractionthe resulting aqueous mixture was extracted with EtOAc and 1 N Na2S2O3
  10. dry with materialThe organic phase was dried over MgSO4, and solvent
  11. customwas removed under reduced pressure
  12. washThe residue eluted through silica gel using 40% EtOAc in hexanes, and solvent
  13. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-b0ee6f31b82e47729e2f163a0a7aba76
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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