Tetrahydrofuran → HCID 15614938, compound

HRID 620364Notes

Reaction equation

HRID 620364 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:14])[F:13])[C:3]=1C(O)=O.[CH2:21]([O:23][C:24]([N:26]=[C:27]=NC(C)(C)C)=[O:25])[CH3:22].[O:33]1CCCC1>>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:14])([F:13])[F:15])[C:3]=1[C:27]([NH:26][C:24]([O:23][CH2:21][CH3:22])=[O:25])=[O:33]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 13839325HCID 13839325, compoundHCID 15614957HCID 15614957, compound

Product 1

HCID 15614938HCID 15614938, compound

Procedure

According to the procedure of O. Mitsunobu et al, Bull. Chem. Soc., Japan, 45, 3607 (1972), a solution of 2-bromo-6-methoxy-5-trifluoromethyl-1-naphthoic acid (4.50 g, 12.9 mmol, prepared by the process of Step 2, Example (11), and ethoxycarbonyl-t-butylcarbodiimide (2.40 g, 14.1 mmol) in dry tetrahydrofuran (80 mL) was heated to reflux under a dry nitrogen atmosphere for 21/3 hours. The THF was removed and the residue was dissolved in chloroform and the solvent evaporated. The resultant solid was triturated with ether (2×5 mL) and dried in vacuo to provide the title compound as an off white solid (4.61 g, 85%), m.p. 169°-171° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a dry nitrogen atmosphere for 21/3 hours
  3. customThe THF was removed
  4. dissolutionthe residue was dissolved in chloroform
  5. customthe solvent evaporated
  6. customThe resultant solid was triturated with ether (2×5 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7a5d673c075143adaf2f3c2effd1c732
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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