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Carbon tetrabromide → 7-(3,3-dibromo-1-pentyl-allyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 899300
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 899300
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([O:29][C:30]([N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([CH:42]([CH:48]=O)[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:40]=2)[C:35]([CH3:51])([CH3:50])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([O:29][C:30]([N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([CH:42]([CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:48]=[C:1]([Br:5])[Br:2])[CH:40]=2)[C:35]([CH3:50])([CH3:51])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 865890267-(1-formyl-hexyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 865890277-(3,3-dibromo-1-pentyl-allyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterAusbeute 31,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of carbon tetrabromide (0.32 g, 0.96 mmole) in 5 mL of dichloromethane, at −20° C., was added triphenyl phosphine in 5 mL of dichloromethane. After stirring at 0° C. for 15 minutes reaction mixture was treated with a solution of 7-(1-formyl-hexyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.18 g, 0.48 mmole, from Example 5 step 8) in 2 mL of dichloromethane. The reaction mixture was stirred at room temperature for 4 hours, quenched by the successive addition of 5 mL of water and 1.5 mL of saturated sodium bicarbonate. The phases were separated and aqueous phase was extracted with two 25 mL portions of dichloromethane. Organic phase was dried over MgSO4, filtered and concentrated in vacuo affording a brownish thick oil. The product was purified by flash chromatography (SiO2, 20% ethyl acetate in hexanes) to yield 0.08 g of 7-(3,3-dibromo-1-pentyl-allyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as a colourless oil.

Aufarbeitung

  1. customreaction mixture
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. customquenched by the successive addition of 5 mL of water and 1.5 mL of saturated sodium bicarbonate
  4. customThe phases were separated
  5. extractionaqueous phase was extracted with two 25 mL portions of dichloromethane
  6. dry with materialOrganic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customaffording a brownish thick oil
  10. customThe product was purified by flash chromatography (SiO2, 20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c0281d92846c439e8cfac3d9b21fe11d
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07354931B2

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