Pyridine → (1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid

HRID 1808001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808001
[OH:1][C@H:2]1[CH2:7][C@H:6]([CH3:8])[CH2:5][CH2:4][C@H:3]1[C:9]([OH:11])=[O:10].N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClCCl>[C:18]([O:1][C@H:2]1[CH2:7][C@H:6]([CH3:8])[CH2:5][CH2:4][C@H:3]1[C:9]([OH:11])=[O:10])(=[O:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 45084907(1r,2s,4r)-2-Hydroxy-4-methylcyclohexanecarboxylic acid

Produkt 1

HCID 57457642(1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acidAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1R,2S,4R)-2-Hydroxy-4-methyl-cyclohexanecarboxylic acid (162 mg, 1.02 mmol) in dichloromethane (5 ml) was added pyridine (495 ul, 6.12 mmol) followed by acetic anhydride (385 ul, 4.08 mmol). The reaction mixture was stirred for 20 h at room temperature. Then, the solvents were removed and 10 ml of 3N HCl solution was added. This mixture was stirred for 30 minutes and then a saturated solution of NaHCO3 was slowly added until PH=9-10. This solution was then extracted with ethyl acetate (2×5 ml). The aqueous phase was then acidified with a 10% HCl solution and extracted with ethyl acetate (3×5 ml). The following ethyl acetate layers were combined, dried (Na2SO4) and concentrated to obtain 109 mg (53%) of (1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid.

Aufarbeitung

  1. customThen, the solvents were removed
  2. addition10 ml of 3N HCl solution was added
  3. stirringThis mixture was stirred for 30 minutes
  4. additiona saturated solution of NaHCO3 was slowly added until PH=9-10
  5. extractionThis solution was then extracted with ethyl acetate (2×5 ml)
  6. extractionextracted with ethyl acetate (3×5 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-44200983232549efbc5363f2df04bb12
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357718B2

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