1,1,1-Trifluoro-2-propanol → HCID 86623616, compound

HRID 1820979Notes

Reaction equation

HRID 1820979 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]([OH:5])[CH3:4].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:19]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[C:22]([C:23]([O:25]C)=[O:24])=[CH:21][N:20]=1>C1COCC1.CCOC(C)=O>[F:32][C:29]([F:30])([F:31])[C:27]1[C:22]([C:23]([OH:25])=[O:24])=[CH:21][N:20]=[C:19]([O:5][CH:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])[CH:28]=1

Participants

6

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinate

Product 1

HCID 86623616HCID 86623616, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 180 mg (1.56 mmol) of 1,1,1-trifluoro-2-propanol in 10 mL of THF at −78° C. was added 1.56 mL (1.56 mmol) of sodium bis(trimethylsilyl)amide (1.0M in THF). After 30 min at −78° C., 250 mg (1.04 mmol) of methyl 6-chloro-4-(trifluoromethyl)nicotinate was added. The reaction mixture was gradually warmed up to rt and stirred over night. The mixture was diluted with 10 mL of EtOAc and washed with brine. The organic layer was dried over MgSO4 and concentrated. Purification using HPLC B gave 160 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.57 (d, J=6.6, 3H), 5.91 (m, 1H), 7.26 (s, 1H), 8.98 (s, 1H).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customPurification

Sources & evidence

ORD record
ord-e02e895af9ee4e8f962255a013d3f305
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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