Isopropanol → HCID 59438527, compound

HRID 2177509Notes

Reaction equation

HRID 2177509 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[OH:14].[CH3:16][CH:17](O)[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[OH-].[Na+]>O1CCCC1>[CH:17]([O:14][C:5]1[CH:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:2])=[O:15])([CH3:18])[CH3:16]

Participants

7

Reactant 5

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 97268Di-tert-butyl azodicarboxylateHCID 349235methyl 2-hydroxy-4-(trifluoromethyl)benzoate

Product 1

HCID 59438527HCID 59438527, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 500 mg (2.271 mmol) 2-hydroxy-4-trifluoromethyl-benzoic acid methyl ester (CAS: 345-28-8), 209 ul (2.725 mmol) 2-propanol and 706.2 mg (2.612 mmol) triphenylphosphine in 6.5 ml tetrahydrofuran under nitrogen at 0° C., was added dropwise a solution of 575.2 mg (2.498 mmol) di-tert-butyl azodicarboxylate in 1 ml tetrahydrofuran. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 hours. 8 ml (15.9 mmol) 2N NaOH was added and the reaction mixture was warmed at 80° C. for 5 hours. The reaction mixture extracted twice with 5 ml ether. The aqueous layer was acidified under ice bath cooling with a 5N HCl solution to pH 1. The resulting precipitate was filtered and dried in vacuo to provide 444 mg (y: 78.8%) of the expected compound as a white solid. MS (m/e): 247.0 (MH+).

Workup

  1. temperaturethe reaction mixture was warmed at 80° C. for 5 hours
  2. extractionThe reaction mixture extracted twice with 5 ml ether
  3. temperaturecooling with a 5N HCl solution to pH 1
  4. filtrationThe resulting precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-026d64732ce24d0fb7f801219b2749bf
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

Loading…