Pyridine → HCID 57457642, compound

HRID 73198Notes

Reaction equation

HRID 73198 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 57457642HCID 57457642, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-19ebc25bf2664683987d21ee310a929c
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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