Dicyclohexylcarbodiimide → HCID 21030583, compound

HRID 1829594Notes

Reaction equation

HRID 1829594 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:3]1.C[Mg]Cl.CC1(C)CCCC(C(=O)C)C1.[C:27]([O:31][CH2:32][C:33](O)=[O:34])(=[O:30])[CH2:28][CH3:29].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:27]([O:31][CH2:32][C:33]([O:11][C:8]([CH:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:12])([CH3:1])[CH2:3]1)([CH3:10])[CH3:9])=[O:34])(=[O:30])[CH2:28][CH3:29]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 913881-(3,3-Dimethylcyclohexyl)ethanoneHCID 12136775(Propionyloxy)acetic acidHCID 22053304HCID 22053304, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 21030583HCID 21030583, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-dimethyl-aminopyridine (122 mg, 1.0 mmol) and 2-(3,3-dimethylcyclohexyl)-2-propanol (2.6 g, 15 mmol), [which is obtainable from methylmagnesium chloride and 1-(3,3-dimethylcyclohexyl)-ethanone by a Grignard reaction] are added successively to a solution of 81% (propionyloxy) acetic acid (2.7 g, 16.5 mmol) in CH2Cl2 (15 ml). The reaction solution is now cooled to 0° C. and dicyclohexylcarbodiimide (3.4 g, 16.5 mmol), dissolved in CH2Cl2 (5 ml) is added. After 1 h at 0° C., the cooling is removed, and the reaction mixture is stirred for a further 16 h at room temperature. The precipitate that has precipitated is, then, filtered off, and the filtrate is freed from solvent in a rotary evaporator. The resulting crude product is taken up in n-pentane (20 ml) and the precipitate that forms is again filtered off. The filtrate is also washed twice with 0.5 M HCl and twice with saturated NaHCO3 solution, and the organic phase is then dried over Na2SO4, filtered off, and concentrated in a rotary evaporator. After purification by flash chromatography (cyclohexane/EtOAc=10:1, Rf=0.23) and subsequent bulb tube distillation (BTD: 221° C., 1.3 mbar), 3.1 g (73%) 2-[1-(3,3-dimethylcyclohexyl)-1-methylethoxy]-2-oxoethyl propionate is obtained as a colorless liquid.

Workup

  1. additionis added
  2. customthe cooling is removed
  3. customThe precipitate that has precipitated
  4. filtrationfiltered off
  5. customthe filtrate is freed from solvent in a rotary evaporator
  6. filtrationthe precipitate that forms is again filtered off
  7. washThe filtrate is also washed twice with 0.5 M HCl and twice with saturated NaHCO3 solution
  8. dry with materialthe organic phase is then dried over Na2SO4
  9. filtrationfiltered off
  10. concentrationconcentrated in a rotary evaporator
  11. customAfter purification
  12. distillationby flash chromatography (cyclohexane/EtOAc=10:1, Rf=0.23) and subsequent bulb tube distillation (BTD: 221° C., 1.3 mbar)

Sources & evidence

ORD record
ord-d7e05e805e144950b3a408743f55b086
Source dataset
uspto-grants-2006_06
Patent number
US07064102B2

Reaction notes

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