Tetrahydrofuran → HCID 15614950, compound

HRID 620349Notes

Reaction equation

HRID 620349 reaction equation
[F: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].C1C[O:36]CC1>>[F: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]=1[C:27]([NH:26][C:24](=[O:25])[O:23][CH2:21][CH3:22])=[O:36]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 13839325HCID 13839325, compoundHCID 15614934HCID 15614934, compound

Product 1

HCID 15614950HCID 15614950, compound

Procedure

According to the procedure of O. Mitsunobu et al, Bull. Chem. Soc. Japan, 45, 3607 (1972), a solution of 2-fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthoic acid (2.30 g, 8.00 mmol, prepared by the process of Example 10), and ethoxycarbonyl-t-butylcarbodiimide (1.50 g, 1.1 eq) in anhydrous THF (40 mL) was heated to reflux for 21/2 hours under a dry nitrogen atmosphere. The reaction was cooled to room temperature and the THF was removed. The crude product was triturated with ether to provide the title compound as an off white solid (2.37 g, 82%). A small sample was recrystallized from CHCl3 :petroleum ether for analysis, m.p. 172°-174° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 21/2 hours under a dry nitrogen atmosphere
  3. customthe THF was removed
  4. customThe crude product was triturated with ether

Sources & evidence

ORD record
ord-d2eea82ca8024102b747e37639c45483
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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