Ethyl Acetate → HCID 15055891, compound

HRID 1199271Notes

Reaction equation

HRID 1199271 reaction equation
[OH:1][C@H:2]([C@H:12]([OH:21])[C@H:13]([OH:20])[C:14]#[C:15][C:16]#[C:17][C:18]#[CH:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[C:22](OCC)(=O)C>C(OCC)C>[OH:1][C@H:2]([C@H:12]([OH:21])[C@H:13]([OH:20])[C:14]#[C:15][C:16]#[C:17][C:18]#[CH:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:22])=[O:10]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 15055890HCID 15055890, compound

Product 1

HCID 15055891HCID 15055891, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A quantity of a 1 mg/ml solution in ethyl acetate of 8(S),9(S),10(R)-trihydroxy-11,13,15-hexadecatriynoic acid (10 ml, 34.2 μmols) was stirred at ambient temperature in a flask equipped with a vacuum adapter. A solution of CH2N2 in diethyl ether (1 ml) was added and the progress of the reaction followed by thin layer chromatography. After 10 minutes, vacuum was applied and the excess CH2N2 was removed. The mixture was partially concentrated to 0.2 ml and applied to a short silica gel column. The desired material was eluted with diethyl ether. After partial concentration, the solvent was replaced by repeated removal of CDCl3 under reduced pressure and the reaction quantized by nmr spectroscopy (using an internal standard) to establish recovery of the title compound (6.8 mg, 65%). Structure assignment was supported by the nmr spectrum.

Workup

  1. customequipped with a vacuum adapter
  2. customthe excess CH2N2 was removed
  3. concentrationThe mixture was partially concentrated to 0.2 ml
  4. washThe desired material was eluted with diethyl ether
  5. concentrationAfter partial concentration
  6. customthe solvent was replaced by repeated removal of CDCl3 under reduced pressure

Sources & evidence

ORD record
ord-941ea4c1a6b04ef0a5d9c017a818e627
Source dataset
uspto-grants-1990_02
Patent number
US04898853

Reaction notes

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