Oxalyl chloride → alpha(R)-Methylcyclohexanepropionic acid chloride

HRID 1379592Notes

Reaction equation

HRID 1379592 reaction equation
[CH3:1][C@H:2]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3](O)=[O:4].C(Cl)(=O)C([Cl:16])=O>CN(C=O)C>[CH3:1][C@H:2]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([Cl:16])=[O:4]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 22877219(2R)-3-cyclohexyl-2-methylpropanoic acid

Product 1

HCID 10888712alpha(R)-Methylcyclohexanepropionic acid chlorideYield 98.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a solution of α(R)-methylcyclohexane-propionic acid (2.4 g, 14 mmol) in dry CH2Cl12 (30 mL) was added DMF (1 drop) and oxalyl chloride (2 g, 15 mmol). After 2 h at room temperature, the mixture was concentrated. The residue was dissolved in Et2O (10 mL). This solution was filtered. The filtrate was concentrated to provide α(R)-methylcyclohexanepropionic acid chloride as a clear yellow liquid (2.6 g, 98% yield). 1H NMR (400 MHz, CDCl3) 3.02-2.91 (m, 1H), 1.80-1.63 (m, 6H), 1.39-1.10 (m, 5H), 1.28 (d, J=7 Hz, 3H), 0.99-0.85 (m, 2H). This material was used without further purification in the coupling reaction described in the following example.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in Et2O (10 mL)
  3. filtrationThis solution was filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bd93828950ee4093998b5867a6893876
Source dataset
uspto-grants-1997_09
Patent number
US05672586

Reaction notes

Loading…