Triethylamine → HCID 57594351, compound

HRID 222909Notes

Reaction equation

HRID 222909 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[OH-].[Na+].FC(F)(F)C(OC1[C:29]([F:30])=[C:28]([F:31])[C:27]([F:32])=[C:26]([F:33])[C:25]=1[F:34])=O.C(N(CC)CC)C>CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8][C:9]1[C:29]([F:30])=[C:28]([F:31])[C:27]([F:32])=[C:26]([F:33])[C:25]=1[F:34])=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 21956805Methyl 3-cyano-4-isopropoxybenzoate

Product 1

HCID 57594351HCID 57594351, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

20.5 g (0.093 mol) of methyl 3-cyano-4-isopropoxybenzoate 4 was dissolved in 200 mL of a 6:4 mixture of methanol and water. To this was added 5.61 g (0.14 mol) of NaOH and the mixture stirred for 2 hours at room temperature. The solution was then filtered through a silica gel plug and the solvents removed under vacuum. The resulting solid was re-dissolved in 200 mL of CH2Cl2 and treated with 19.3 mL (0.11 mol) of perfluorophenyl 2,2,2-trifluoroacetate 5 and 19.5 mL (0.14 mol) of triethylamine. After stirring overnight, the solution was filtered and any solids rinsed with CH2Cl2. The combined organic fractions were run through a short silica gel column and then evaporated to dryness to give 29 g (83.5% yield) of 6 which was characterized by LCMS and HNMR.

Workup

  1. filtrationThe solution was then filtered through a silica gel plug
  2. customthe solvents removed under vacuum
  3. dissolutionThe resulting solid was re-dissolved in 200 mL of CH2Cl2
  4. stirringAfter stirring overnight
  5. filtrationthe solution was filtered
  6. washany solids rinsed with CH2Cl2
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-59ba08cbd6aa4403a9e55b9e4e2cab7e
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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