Benzoyl chloride → 1,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl ester

HRID 442657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442657
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.Cl[Sn](Cl)(Cl)Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC.CCOC(C)=O>[C:20]([C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 24287Tin tetrachlorideHCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 4069581,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl esterAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 3,4-methylenedioxyphenylacetate (150 mg, 0.77 mmol) in CH2Cl2 (5 mL) was added SnCl4 (1.0M solution in CH2Cl2 ; 1.5 mL, 1.5 mmol) at 0° C. Then benzoyl chloride (130 μL, 1.1 mmol) was added. The reaction mixture was allowed to warm slowly to room temperature. After 24 h, the mixture was added to a saturated NaHCO3 solution (30 mL), diluted with 1:1 hexane/EtOAc (60 mL), washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was separated by chromatography on silica gel (4:1 hexane/EtOAc) to yield the title compound (110 mg, 48%). 1H NMR (CDCl3) 7.78-7.45 (m, 5H), 6.88 (s, 1H), 6.84 (s, 1H), 6.04 (s, 2H), 3.80 (s, 2H), 3.61 (s, 3H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo
  4. customthe resulting residue was separated by chromatography on silica gel (4:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e441c82b165346df89d10a8470b72bed
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891871

Notizen zur Reaktion

Wird geladen…