Sodium Hydroxide → HCID 21883613, compound

HRID 722308Notes

Reaction equation

HRID 722308 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]([F:15])([F:14])[F:13])[C:9]([C:16]([O:18]CC)=[O:17])=[CH:8][C:7]=2[CH:21]=1)#[N:2].[OH-].[Na+]>C1COCC1.C(O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]([F:15])([F:13])[F:14])[C:9]([C:16]([OH:18])=[O:17])=[CH:8][C:7]=2[CH:21]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21883660HCID 21883660, compound

Product 1

HCID 21883613HCID 21883613, compound

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of the ester (Step 2) (0.077 g, 0.259 mmol) in THF-EtOH-H2O (7:2:1, 2 mL) in a 5 mL pear-shaped flask was added aqueous NaOH (0.13 mL, 2.5 N solution) in one portion. After stirring for 6 hours at room temperature the solution was partially concentrated in vacuo to remove most of the THF and EtOH. The resulting solution was diluted with H2O and washed with diethyl ether. The resulting aqueous phase was sparged with nitrogen to remove trace diethyl ether and was acidified with concentrated HCl yielding a sticky suspension. The suspension was extracted with diethyl ether and the ether was dried over MgSO4, filtered and concentrated in vacuo yielding a pale yellow oil. This oil was crystallized from methylene chloride-hexanes yielding the title compound (0.041 g, 59%) as a tan powder: mp 185.1–186.1° C. 1H NMR (acetone-d6/300 MHz) 7.99–7.94 (m, 2H), 7.83 (dd, 1H, J=8.5, 2.0 Hz), 7.25 (d, 1H, J=8.5 Hz), 5.99 (q, 1H, J=7.0 Hz). FABLRMS m/z 270 (M+H). EIHRMS m/z 269.0316 (M+, Calc'd 269.0300).

Workup

  1. concentrationwas partially concentrated in vacuo
  2. customto remove most of the THF and EtOH
  3. additionThe resulting solution was diluted with H2O
  4. washwashed with diethyl ether
  5. customThe resulting aqueous phase was sparged with nitrogen
  6. customto remove trace diethyl ether
  7. extractionThe suspension was extracted with diethyl ether
  8. dry with materialthe ether was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customyielding a pale yellow oil
  12. customThis oil was crystallized from methylene chloride-hexanes yielding the title compound (0.041 g, 59%) as a tan powder

Sources & evidence

ORD record
ord-44df8d9fbf9940ae8d82968a4a53abb4
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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