Triphenylphosphine → HCID 15289612, compound

HRID 326937Notes

Reaction equation

HRID 326937 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O:24][CH2:25][CH3:26])=O.[CH3:32][C:33]([CH3:41])([CH2:39]O)[CH2:34][C:35]([O:37][CH3:38])=[O:36].[S:42]1C=CC=C1CC(O)=O>C1COCC1>[C:25]([S:42][CH2:39][C:33]([CH3:41])([CH3:32])[CH2:34][C:35]([O:37][CH3:38])=[O:36])(=[O:24])[CH3:26]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15289611HCID 15289611, compound

Product 1

HCID 15289612HCID 15289612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine (107.8 g, 0.411 mol) in THF (700 mL) maintained at 0° C. was added dropwise DEAD (diethyl azodicarboxylate) (64.7 mL, 0.411 mol) and the mixture was stirred at 0° C. for 30 min until the complex was precipitated. A solution of the alcohol of Step 8 (30 g, 0.205 mol) and thiolacetic acid (29.4 mL, 0.411 mol) in THF (300 mL) was then added dropwise (mechanical stirring). After 4 days at 4° C. the reaction mixture was evaporated to dryness, the white precipitate was suspended in 30:1 hexane:EtOAc and filtered. The residual oil was then purified by a flash chromatography using toluene then 100:1 toluene:EtOAc to yield the title compound.

Workup

  1. customwas precipitated
  2. stirring(mechanical stirring)
  3. customAfter 4 days at 4° C. the reaction mixture was evaporated to dryness
  4. filtrationEtOAc and filtered
  5. customThe residual oil was then purified by a flash chromatography

Sources & evidence

ORD record
ord-4eee150485a648bba13ef249e5537fb2
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Reaction notes

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