Sodium hydride → HCID 71257376, compound

HRID 2200814Notes

Reaction equation

HRID 2200814 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl[C:13]1[CH:14]=[C:15]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=1)[C:16]([O:18]C(C)(C)C)=[O:17].[H-].[Na+]>O1CCCC1>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:13]3[CH:14]=[C:15]([CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[N:25]=3)[C:16]([OH:18])=[O:17])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 86666515HCID 86666515, compound

Product 1

HCID 71257376HCID 71257376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a vial, 1,4-dioxaspiro[4.5]decan-8-ol (0.400 g, 2.53 mmol) was dissolved in tetrahydrofuran (8.44 mL) with tert-butyl 2-chloro-6-(trifluoromethyl)isonicotinate (0.510 g, 1.81 mmol) and cooled to 0° C. and a 60% mixture of sodium hydride in mineral oil (123 mg, 3.08 mmol) was added and the mixture was stirred for 30 minutes at 0° C. and at 25° C. for 30 minutes at which time TLC analysis showed most of the ester was consumed and a new spot with lower Rf was formed. The reaction was continued for 16 hours. LCMS analysis showed that it consisted mainly of the acid. TLC analysis showed the original product was not present. The reaction was quenched with water and extracted with EtOAc. The crude product was used in the next reaction without further purification. MS (ES): 348 (M+1).

Workup

  1. customwas consumed
  2. customa new spot with lower Rf was formed
  3. waitThe reaction was continued for 16 hours
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc
  6. customThe crude product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-ce91f498834747ac9d9cb2f9b778613f
Source dataset
uspto-grants-2016_06
Patent number
US09359358B2

Reaction notes

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