Triphenylphosphine → HCID 54247816, compound

HRID 1974503Notes

Reaction equation

HRID 1974503 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:15]=[C:16]([C:20]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)([O:23][CH3:24])[CH2:21][CH3:22])[CH:17]=[CH:18][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]=[CH:56][CH2:57]O)[CH:50]=1.C(O)=CC>O1CCCC1>[N:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]=[CH:56][CH2:57][O:13][C:14]2[CH:15]=[C:16]([C:20]([C:25]3[S:26][CH:27]=[CH:28][N:29]=3)([O:23][CH3:24])[CH2:21][CH3:22])[CH:17]=[CH:18][CH:19]=2)[CH:50]=1

Participants

7

Reactant 5

HCID 11776Triphenylphosphine2×HCID 143500HydroxypropyleneHCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 35635042-Propen-1-ol, 3-(3-pyridinyl)-HCID 156373793-[1-Methoxy-1-(1,3-thiazol-2-yl)propyl]phenol

Product 1

HCID 54247816HCID 54247816, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.38 ml) was added dropwise to a mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (0.37 g), triphenylphosphine (0.57 g), 3-(3-pyridyl)prop-2-en-1-ol (0.27 g) and tetrahydrofuran (7 ml) which had been cooled to 0°-5° C. in an ice-bath. The mixture was stirred at this temperature range for 2 hours and then at ambient temperature for 4 hours. Further portions of diethyl azodicarboxylate (0.1 ml), triphenylphosphine (0.14 g) and the propenol (0.045 g) were added and the mixture was stirred at ambient temperature for 18 hours. The mixture was partitioned between ethyl acetate (40 ml) and dilute aqueous hydrochloric acid (40 ml). The aqueous layer was separated and basified by adding potassium carbonate portionwise. The resulting solution was extracted with ethyl acetate (3×20 ml). The combined extracts were dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with toluene/ethyl acetate (2/3 v/v) to give 2-[1-[3-(3-(3-pyridyl)prop-2-en-1-yloxy)phenyl]-1-methoxypropyl]thiazole as a colourless oil (0.162 g).

Workup

  1. temperaturehad been cooled to 0°-5° C. in an ice-bath
  2. waitat ambient temperature for 4 hours
  3. stirringthe mixture was stirred at ambient temperature for 18 hours
  4. customThe mixture was partitioned between ethyl acetate (40 ml) and dilute aqueous hydrochloric acid (40 ml)
  5. customThe aqueous layer was separated
  6. additionby adding potassium carbonate portionwise
  7. extractionThe resulting solution was extracted with ethyl acetate (3×20 ml)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. customevaporated
  10. customThe residue was purified by column chromatography
  11. washeluting with toluene/ethyl acetate (2/3 v/v)

Sources & evidence

ORD record
ord-3a37733dfc334c7c8d9e673541536018
Source dataset
uspto-grants-1994_02
Patent number
US05283245

Reaction notes

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