Allyl Alcohol → HCID 18441987, compound

HRID 458431Notes

Reaction equation

HRID 458431 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.[CH3:13][C:14]1(C)[O:21][C:19](=O)[CH2:18][C:16](=O)[O:15]1.C1CCC(N=C=NC2CCCCC2)CC1.C(O)C=C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](=[O:12])[CH2:13][C:14]([O:15][CH2:16][CH:18]=[CH2:19])=[O:21]

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 1235812,4-Difluorophenylacetic acid

Product 1

HCID 18441987HCID 18441987, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (40 mL) solution of 2,4-difluorophenyl acetic acid (6.89 g, 40.03 mmol) at 0° C. was added DMAP (4.89 g, 40.03 mmol), and Meldrum's Acid (5.77 g, 40.03 mmol) followed by DCC (8.26 g, 40.03 mmol). The reaction mixture was warmed to ambient temperature and stirred for 4 h. The reaction was filtered to remove the DCU and the filtrate washed with 1N HCl, H2O, and brine. The organics were dried (Na2SO4), filtered and concentrated to a yellow oil. The residue was redissolved in THF (40 mL) and allyl alcohol (8 mL, 117.63 mmol). The reaction mixture was refluxed for 3 h and then concentrated to deliver 9.67 g (95% yield) of the title compound as a pale yellow oil and used without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.16–7.10 (m, 1H), 6.82 (dd, J=16.6, 8.2 Hz, 2H), 5.91–5.82 (m, 1H), 5.31 (dd, J=17.3, 1.4 Hz, 1H), 5.25 (dd, J=10.3, 1.0 Hz, 1H), 4.61 (d, J=5.8 Hz, 2H), 3.82 (s, 2H), 3.52 (s, 2H).

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the DCU
  3. washthe filtrate washed with 1N HCl, H2O, and brine
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil
  7. dissolutionThe residue was redissolved in THF (40 mL)
  8. temperatureThe reaction mixture was refluxed for 3 h
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-50aab1dc991c42f8b51b75b13479888a
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

Loading…