Dimethylformamide → Benzyl 2,2-dimethylpent-4-enoate

HRID 1367135

Reaktionsgleichung

Reaktionsgleichung von HRID 1367135
C([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]([CH3:15])([CH2:12][CH:13]=[CH2:14])[C:9]([OH:11])=[O:10].CN(C=O)C.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.C(OCC)C>[CH3:7][C:8]([CH3:15])([CH2:12][CH:13]=[CH2:14])[C:9]([O:11][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:10]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1400652,2-Dimethyl-4-pentenoic acid

Produkt 1

HCID 66973286Benzyl 2,2-dimethylpent-4-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a mixture of K2CO3 (1.58 g, 11.5 mmol), 2,2-dimethylpent-4-enoic acid (1.30 g, 10.1 mmol) and DMF (8.1 mL) was added benzyl bromide (1.40 g, 8.19 mmol) slowly over 15 minutes. After 4 hours the mixture was diluted with a mixture of water (80 mL) and diethylether (80 mL). The organic layer was separated and sequentially washed with 80 mL of 5% aqueous sodium bicarbonate, saturated copper sulfate, slightly acidic water, half-saturated brine, and then saturated brine. The organics were then dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound which was used without further purification. MS: m/z=219 (M+1).

Aufarbeitung

  1. customThe organic layer was separated
  2. washsequentially washed with 80 mL of 5% aqueous sodium bicarbonate, saturated copper sulfate, slightly acidic water, half-saturated brine
  3. dry with materialThe organics were then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cd97e3c55a20408a8983128802fb236d
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893079B2

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