Tetrahydrofuran → Ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate

HRID 31749

반응식

HRID 31749 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.C1COCC1.[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21]C([O-])=O.[K+].[Cl-].[Mg+2].[Cl-]>C(Cl)(=O)C(Cl)=O.CN(C=O)C.C(#N)C.C(N(CC)CC)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:12])[CH2:21][C:20]([O:26][CH2:27][CH3:28])=[O:25])=[CH:13][CH:14]=1

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 3446434Potassium ethyl malonateHCID 51387914-(Fur-2-yl)benzoic acidHCID 5360315Magnesium Chloride

생성물 1

HCID 22142724Ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 6342Acetonitrile용매2회HCID 8471Triethylamine용매2회HCID 65578Oxalyl chloride용매2회

실험 절차

The acid from Step 1 was converted to the acid chloride by refluxing in a mixture of oxalyl chloride (1.3 ml), THF (20 ml) and several drops of DMF. Small portions of oxalyl chloride were added until the reaction was homogeneous. Reflux continued for 0.5 hours, then the solvent was removed in vacuo to give the crude acid chloride. Meanwhile, potassium ethyl malonate (2.7 g) was reacted with anhydrous magnesium chloride (1.9 g) and triethylamine (2.21 ml) in dry acetonitrile (50 ml) at room temperature for 3 hours. Triethylamine (1 ml) was added, followed by addition of a solution of the acid chloride in acetonitrile. The mixture was then stirred overnight at room temperature, then concentrated to dryness. The residue was partitioned between toluene and 10% aqueous HCl. The organic layer was washed with 10% HCl and water, dried and was then concentrated to give crude ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate as a solid.

후처리

  1. temperatureReflux
  2. customthe solvent was removed in vacuo
  3. customto give the crude acid chloride
  4. concentrationconcentrated to dryness
  5. customThe residue was partitioned between toluene and 10% aqueous HCl
  6. washThe organic layer was washed with 10% HCl and water
  7. customdried
  8. concentrationwas then concentrated

출처 및 근거

ORD 기록
ord-825e1fd4f92d46999bb219a64ae09682
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425557B2

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