Tetrahydrofuran → HCID 15614953, compound

HRID 620362Notes

Reaction equation

HRID 620362 reaction equation
[Cl: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>>[Cl: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:13])[F:14])[C:3]=1[C:27]([NH:26][C:24](=[O:25])[O:23][CH2:21][CH3:22])=[O:33]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 13839325HCID 13839325, compoundHCID 15614961HCID 15614961, compound

Product 1

HCID 15614953HCID 15614953, compound

Procedure

A solution of 2-chloro-6-methoxy-5-(trifluoromethyl)naphthoic acid (3.50 g, 11.5 mmol, prepared by the process of Example 14), and ethoxycarbonyl-t-butylcarbodiimide (2.2 g, 1.1 eq) in dry tetrahydrofuran (58 mL) was heated to reflux under a dry nitrogen atmosphere for 51/2 hours. The tetrahydrofuran was removed and the resultant solid was triturated with ether (2×15 mL) and dried in vacuo. A second crop was recovered from the ether and combined with the product (3.36 g, 78%). The small sample was further purified by flash chromatography (70/30 petroleum ether/ethyl acetate) to provide the analytically pure product as a white solid, m.p. 169°-171° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a dry nitrogen atmosphere for 51/2 hours
  3. customThe tetrahydrofuran was removed
  4. customthe resultant solid was triturated with ether (2×15 mL)
  5. customdried in vacuo
  6. customA second crop was recovered from the ether
  7. customThe small sample was further purified by flash chromatography (70/30 petroleum ether/ethyl acetate)
  8. customto provide the analytically pure product as a white solid, m.p. 169°-171° C.

Sources & evidence

ORD record
ord-59550d4b26a84d8f85bdacd1953bb20b
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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