Allyl Alcohol → HCID 86598942, compound

HRID 1296693Notes

Reaction equation

HRID 1296693 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:26][CH:25]=3)=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH2:38](O)[CH:39]=[CH2:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1.C(Cl)Cl>[CH2:40]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][CH2:36][CH2:37]4)=[CH:26][CH:25]=3)=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=3)[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1)[CH:39]=[CH2:38]

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10152439HCID 10152439, compound

Product 1

HCID 86598942HCID 86598942, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 7-hydroxy-4-{(4-(2-pyrrolidinylethoxy)phenyl)methyl}-3-(4-(trifluoromethyl)phenyl)-2H-chromen-2-one (0.550 g.) in tetrahydrofuran (6 mL) and methylene chloride (6 mL) was added allyl alcohol (0.226 mL) and triphenylphosphine (0.641 g.). Diisopropylazodicarboxylate (0.437 mL) was then added dropwise to the solution. The resultant mixture was allowed to stir for about one hour (or until the starting material was consumed). The solution was concentrated under reduced pressure and extracted with methylene chloride (3×) and water. The organic layers were dried over magnesium sulfate, the magnesium sulfate was filtered and the solvent was concentrated under reduced pressure to provide an orange oil. The oil was purified via silica gel chromatography (6–10% methanol/methylene chloride) to afford 7-prop-2-enyloxy-4-{(4-(2-pyrrolidinylethoxy)phenyl)methyl}-3-(4-(trifluoromethyl) Phenyl)-2H-chromen-2-one (0.245 g., 40% yield). MS (m/z) 550 (M+1)+.

Workup

  1. customwas consumed)
  2. concentrationThe solution was concentrated under reduced pressure
  3. extractionextracted with methylene chloride (3×) and water
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. filtrationthe magnesium sulfate was filtered
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customto provide an orange oil
  8. customThe oil was purified via silica gel chromatography (6–10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-41664f051bd3460abbfb84188f219170
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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