2-Methyl-2-pentene → 5-bromo-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 1886808

Reaktionsgleichung

Reaktionsgleichung von HRID 1886808
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]/[O:12]C)/[CH2:6][CH2:5]2.CC(=CCC)C.Cl([O-])=[O:21].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]([OH:12])=[O:21])[CH2:6][CH2:5]2

Komponenten

7

Edukt 4

HCID 122432-Methyl-2-penteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 58909702(E)-5-bromo-1-(methoxymethylene)-2,3-dihydro-1H-indene

Produkt 1

HCID 138400065-bromo-2,3-dihydro-1H-indene-1-carboxylic acidAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a solution of the product from Example 70, Part B (300 mg, 1.3 mmol) and 2-methyl-2-pentene (8 ml) in tert-butanol (32 ml) was added a solution of sodium chlorite (1.36 g, 0.12 mmol) in H2O (12 ml) containing sodium dihydrogen phosphate (1.07 g, 8.9 mmol) and the mixture was stirred vigorously for 20 min at room temperature. Solvents were concentrated in vacuo and the residue was diluted with H2O, extracted with EtOAc (3×), extracts combined, dried (Na2SO4), and concentrated in vacuo to give the title compound (180 mg, 56%).

Aufarbeitung

  1. concentrationSolvents were concentrated in vacuo
  2. additionthe residue was diluted with H2O
  3. extractionextracted with EtOAc (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-75c4b468788f4d2baf69c7bc7896bbe3
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501238B2

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