Piperidine → 2-(3-((1-Ethoxy-2-methyl-1-oxopropan-2-yl)oxy)phenyl)acetic acid

HRID 480711Notes

Reaction equation

HRID 480711 reaction equation
C([O:4][C:5]([CH2:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][C:12]([CH3:19])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:6])C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCCCC1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([O:15][C:13]([C:12]([CH3:18])([O:11][C:10]1[CH:9]=[C:8]([CH2:7][C:5]([OH:6])=[O:4])[CH:22]=[CH:21][CH:20]=1)[CH3:19])=[O:14])[CH3:17]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 18766532Ethyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

Product 1

HCID 187665702-(3-((1-Ethoxy-2-methyl-1-oxopropan-2-yl)oxy)phenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[3-(allyloxycarbonylmethyl)phenoxy]-2-methylpropionate (6.40 g, 20.9 mmol) was dissolved in tetrahydrofuran (150 mL). Subsequently, triphenylphosphine (2.42 g, 2.09 mmol) and piperidine (41.34 mL, 41.8 mmol) were added thereto. Under argon atmosphere, tetrakis(triphenylphosphine)palladium (2.42 g, 2.09 mmol) was added, the resultant mixture was stirred for three hours at room temperature. After completion of reaction, the reaction mixture was concentrated under reduced pressure, followed by addition of chloroform and washing sequentially with 3M hydrochloric acid, water, and saturated brine. The resultant mixture was subjected to drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol/acetic acid=50/1/0.5), whereby the target compound was obtained (6.88 g, 25.84 mmol, >q.).

Workup

  1. customAfter completion of reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionfollowed by addition of chloroform
  4. washwashing sequentially with 3M hydrochloric acid, water, and saturated brine
  5. dry with materialto drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol/acetic acid=50/1/0.5), whereby the target compound
  6. customwas obtained (6.88 g, 25.84 mmol, >q.)

Sources & evidence

ORD record
ord-a16490dc568b4715a8b592f42156dcf5
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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