Triphenylphosphine → HCID 86747637, compound

HRID 486737Notes

Reaction equation

HRID 486737 reaction equation
[C:1]([C@H:3]1[C@H:7]([CH2:8]O)[S:6][CH2:5][CH2:4]1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:41]([OH:44])(=[S:43])[CH3:42].C(=O)(O)[O-].[Na+]>C1COCC1>[C:41]([S:43][CH2:8][C@@H:7]1[S:6][CH2:5][CH2:4][C@H:3]1[C:1]#[N:2])(=[O:44])[CH3:42]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 5462977Diethyl azodicarboxylateHCID 67753893HCID 67753893, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86747637HCID 86747637, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of trans-4-cyano-5-hydroxymethyltetrahydrothiophene (78 mg) and triphenylphosphine (283 mg) in THF (3 ml), diethylazodicarboxylate (188 mg) dissolved in THF (1.2 ml) and thioacetic acid (82 mg) dissolved in THF (1.2 ml) were added dropwise under ice-cooling and the mixture was stirred for 30 minutes. Saturated aqueous sodium bicarbonate solution was added to the mixture and extracted with diethylether. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 94 mg (86%) of trans-5-acetylthiomethyl-4-cyanotetrahydrothiophene.

Workup

  1. additionwere added dropwise under ice-
  2. temperaturecooling
  3. extractionextracted with diethylether
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-9559794e80984df7978dd2eea220ace8
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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