Triphenylphosphine → HCID 57182805, compound

HRID 2209547Notes

Reaction equation

HRID 2209547 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC([O:24][CH:25]([CH3:27])C)=O.[C:34]([S:38][C@@H:39]([CH3:42])[CH2:40]O)([CH3:37])([CH3:36])[CH3:35].[S:43]1C=CC=C1CC(O)=O>C1COCC1>[C:25]([S:43][CH2:40][C@@H:39]([S:38][C:34]([CH3:37])([CH3:36])[CH3:35])[CH3:42])(=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57285352HCID 57285352, compound

Product 1

HCID 57182805HCID 57182805, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3.54 g of triphenylphosphine in 50 mL of THF at 0° C. was added 2.66 mL of diisopropyl azodicarboxylate. The mixture was stirred for an additional 30 min. To the resulting white precipitate was added 1.00 g of (2S)-2-(t-butylthio)-1-propanol in 5 mL of THF. The reaction mixture was stirred for 10 min, then 0.966 mL of thiolacetic acid was added and stirring was continued at 0° C. for 1 h and at room temperature for 1 h. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (5% CH2Cl2 in hexane) to give 1.16 g of (2S)-1-(acetylthio)-2-(t-butylthio)propane as an oil at 83% yield. Characteristic analytical data are as follows: 1H NMR (300 MHz, CDCl3) δ3.32 (m, 1H), 2.8-2.94 (m, 2H), 2.35 (s, 3 H), 1.38 (s, 9H), 1.33 (d, J=7 Hz, 3H).

Workup

  1. stirringThe reaction mixture was stirred for 10 min
  2. stirringstirring
  3. waitwas continued at 0° C. for 1 h and at room temperature for 1 h
  4. customThe solvent was evaporated under vacuum
  5. customthe residue was purified by flash chromatography (5% CH2Cl2 in hexane)

Sources & evidence

ORD record
ord-29e394ee873a4e0aa94ed19cbf17bd57
Source dataset
uspto-grants-1995_10
Patent number
US05455262

Reaction notes

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