Allyl Alcohol → Allyl 4-(4-fluorophenyl)-3-oxobutanoate

HRID 458425Notes

Reaction equation

HRID 458425 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH3:12][C:13]1(C)[O:20][C:18](=O)[CH2:17][C:15](=O)[O:14]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:3]=[CH:4][C:5]([CH2:8][C:9](=[O:11])[CH2:12][C:13]([O:14][CH2:15][CH:17]=[CH2:18])=[O:20])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 98372-(4-Fluorophenyl)acetic acidHCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 18441988Allyl 4-(4-fluorophenyl)-3-oxobutanoateYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (210 mL) solution of 4-fluorophenyl acetic acid (32.28 g, 209.42 mmol) at 0° C. was added DMAP (25.58 g, 209.42 mmol), and Meldrum's Acid (30.18 g, 209.42 mmol) followed by DCC (43.21 g, 209.42 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 (200 mL) and allyl alcohol (14.38 mL, 211.51 mmol). The reaction mixture was refluxed for 3 h and then concentrated to deliver 47 g (95% yield) of the title compound as a pale yellow oil and used without further purification.

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 (200 mL)
  8. temperatureThe reaction mixture was refluxed for 3 h
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-972165515bc042b7b365ec30344c51e0
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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