Triethylamine → HCID 86691792, compound

HRID 713544Notes

Reaction equation

HRID 713544 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[CH2:6][C:7]1([OH:12])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C.[C:29](Cl)(=[O:33])[C:30]([CH3:32])=[CH2:31]>C(Cl)Cl>[C:29]([O:12][C:7]1([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:20])([F:21])[F:1])[CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:13]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1)(=[O:33])[C:30]([CH3:32])=[CH2:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 86691793HCID 86691793, compound

Product 1

HCID 86691792HCID 86691792, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

43 g of 1-(3,5-bis(trifluoromethyl)benzyl)cyclopentanol and 16.7 g of triethylamine dissolved in 100 mL of methylene chloride was slowly charged into flask equipped with magnetic stirrer and 14.93 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 the rotary evaporator affording 34 g of 1-(3,5-bis(trifluoromethyl)benzyl)cyclopentyl methacrylate (˜65%) yield of as an amber oil. The oil was purified further by passing through a silica gel plug eluting with a 60/40 mixture of hexanes/methylene chloride affording 30 g of 1-(3,5-bis(trifluoromethyl)benzyl)cyclopentyl methacrylate (LG1) as pure product. 1H NMR (500 MHz, Acetone-d6): δ 7.97 (s, 1H), 7.76 (s, 2H), 5.99 (s, 1H, vinyl), 5.6 (s, 1H, vinyl), 3.56 (s, 2H), 2.23-1.70 (m, 8H), 1.80 (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 the rotary evaporator

Sources & evidence

ORD record
ord-834e914cbecc4c7fbf633bf76ae02aa1
Source dataset
uspto-grants-2015_11
Patent number
US09182662B2

Reaction notes

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