Water → Methyl 1-(5-methylhexyl)cyclopentanecarboxylate

HRID 51065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51065
[CH:1]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26].O>C1COCC1>[CH3:26][CH:25]([CH3:27])[CH2:24][CH2:23][CH2:22][CH2:21][C:1]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 78365Methyl cyclopentanecarboxylateHCID 5207261-Bromo-5-methylhexaneHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 22736519Methyl 1-(5-methylhexyl)cyclopentanecarboxylateAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl cyclopentanecarboxylate (300 mg, 2.3 mmol) in THF (20 ml) at −78° C. was added LHMDS (4.6 mL, 4.6 mmol) and stirred for 30 min, and followed by 1-bromo-5-methylhexane (626 mg, 3.5 mmol). The mixture was stirred from −78° C. to rt over 16 hr, before 30 ml of H2O was added and then was extracted with CH2Cl2 (2×30 mL). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated, then purified using flash chromatography to give an oil (110 mg, 21%). MS [M+H]+333.

Aufarbeitung

  1. additionwas added
  2. extractionwas extracted with CH2Cl2 (2×30 mL)
  3. washThe combined extracts were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-f27a98017a2840df8ead0804d1682c90
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713476B2

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