Tetrahydrofuran → HCID 66868325, compound

HRID 1503188Notes

Reaction equation

HRID 1503188 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Li+].C[C:12](P(OC)(O)=O)([C:14]([O-:16])=[O:15])[CH3:13].[F:22][C:23]([F:35])([F:34])[C:24]1[CH:29]=[CH:28][C:27](C(=O)CC)=[CH:26][CH:25]=1.[CH2:36]1COC[CH2:37]1>[NH4+].[Cl-]>[CH3:1][O:16][C:14](=[O:15])[CH:12]=[C:13]([C:27]1[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:34])[F:35])=[CH:29][CH:28]=1)[CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 136554p-TrifluoromethylpropiophenoneHCID 2733832Lithium HexamethyldisilazideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 66868325HCID 66868325, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a chilled (0° C.) solution of lithium bis(trimethylsilyl)amide (1.0 M, 50 mL) was dropwise added a solution of trimethylphosphonoacetate, keeping the temperature below 10° C. The solution was then allowed to warm to room temperature and stirred for an additional five minutes, after which a solution of 4′-(trifluoromethyl)propiophenone in THF (25 mL) was added in one portion. The solution was slowly heated to 50° C. for eight hours. The solution was cooled to room temperature, then diluted with a 10% NH4Cl solution (100 mL), and extracted with ethyl acetate (2×100 mL). The organic layers were combined and dried over MgSO4, filtered, and the filtrate concentrated to a white solid which was recrystallized from hexane/ethyl acetate to give 5.42 grams of 3-(4-trifluoromethylphenyl)pent-2-enoic acid methyl ester intermediate (85% yield).

Workup

  1. customthe temperature below 10° C
  2. temperatureThe solution was slowly heated to 50° C. for eight hours
  3. temperatureThe solution was cooled to room temperature
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated to a white solid which
  8. customwas recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-aa09d9f66c7e4cf6be3e60dd6bacbff9
Source dataset
uspto-grants-2015_12
Patent number
US09212155B2

Reaction notes

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