Triethylamine → HCID 86691794, compound

HRID 713545Notes

Reaction equation

HRID 713545 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH3:6].C(N(CC)CC)C.[C:23](Cl)(=[O:27])[C:24]([CH3:26])=[CH2:25]>C(Cl)Cl>[C:23]([O:7][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH2:4][CH2:3][C:2]([F:14])([F:15])[F:1])[CH3:6])(=[O:27])[C:24]([CH3:26])=[CH2:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 64567813HCID 64567813, compound

Product 1

HCID 86691794HCID 86691794, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

21 g of 5,5,5-trifluoro-2-phenylpentan-2-ol (5) and 11.6 g of triethylamine dissolved in 40 mL of methylene chloride was slowly charged into flask equipped with magnetic stirrer and 11 ml, of methacryloyl chloride in 100 mL of dichloromethane cooled down to 0° C. The resultant mixture slowly warmed up to room temperature and allowed to stir at this temperature for 12 hours. Upon completion of the reaction as confirmed by thin layer chromatography, the mixture was quenched by pouring into 400 mL of deionized water and extracted further into methylene chloride. The methylene chloride extracts were then dried over sodium sulfate, filtered and concentrated in vacuo affording 20 g of 5,5,5-trifluoro-2-phenylpentan-2-yl methacrylate (LG2) (˜72% yield) of as an amber oil. The oil was purified further by passing through a silica gel plug and eluting with a 70:30 mixture of hexanes/methylene chloride to afford 19 g of pure product. 1H NMR (500 MHz, Acetone-d6): δ 7.32 (s, 3H), 7.24 (s, 2H), 6.11 (s, 1H, vinyl), 5.6 (s, 1H, vinyl), 2.45-2.05 (m/m, 5H), 1.92 (s, 3H), 1.87 (s, 3H).

Workup

  1. additionwas slowly charged into flask
  2. customequipped with magnetic stirrer
  3. customUpon completion of the reaction
  4. customthe mixture was quenched
  5. additionby pouring into 400 mL of deionized water
  6. extractionextracted further into methylene chloride
  7. dry with materialThe methylene chloride extracts were then dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cdd83bfbbc7401cb686475eb9da5ebe
Source dataset
uspto-grants-2015_11
Patent number
US09182662B2

Reaction notes

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