Triphenylphosphine → HCID 86612602, compound

HRID 1784950Notes

Reaction equation

HRID 1784950 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:38]1C=CC=C1CC(O)=O.[CH3:47][CH:48]([O:50]C(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:48]([S:38][CH2:2][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:50])[CH3:47]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 610139Diethyl 5-(hydroxymethyl)isophthalateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 86612602HCID 86612602, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To diethyl 5-(hydroxymethyl)isophthalate (2.52 gm, 10 mmol) in THF (30 ml), triphenyl phosphine (5.25 gm, 20 mmol) was added followed by thiolacetic acid (1.52 gm, 20 mmol) and Diisopropylazodicarboxylate (4.04 gm, 20 mmol) at 0° C. Reaction mixture was then allowed to come to rt and stirred for 2 h. Then solvent was removed, crude was redissolved in minimum amount of CH2Cl2. With stirring, hexane was added and the resultant solids were discarded. Filtrtae was evaporated to dryness and the residue was column purified to yield diethyl 5-(acetylthiomethyl)isophthalate in 95% yield.

Workup

  1. customReaction mixture
  2. customto come to rt
  3. customThen solvent was removed
  4. dissolutioncrude was redissolved in minimum amount of CH2Cl2
  5. stirringWith stirring
  6. additionhexane was added
  7. customFiltrtae was evaporated to dryness
  8. custompurified

Sources & evidence

ORD record
ord-46c4bb24452e4994b14feba19b2a7e91
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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