Methanol → Dimethyl 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]heptanedioate

HRID 1250313Notes

Reaction equation

HRID 1250313 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:5]=1)#[N:2].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].[OH-:24].[CH2:25]([N+](C)(C)C)[C:26]1[CH:31]=CC=CC=1.[CH3:36][OH:37]>C(#N)C>[CH3:23][O:22][C:18](=[O:21])[CH2:19][CH2:20][C:3]([C:1]#[N:2])([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:5]=1)[CH2:25][CH2:26][C:31]([O:37][CH3:36])=[O:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 107282283-(Cyclopentyloxy)-4-methoxyphenylacetonitrile

Product 1

HCID 10811164Dimethyl 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]heptanedioate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
-10 °C

Procedure

A 12 liter round bottom flask equipped with an overhead stirrer, internal thermometer, and a reflux condensor equipped with a nitrogen inlet was flushed with nitrogen. The flask was charged with a solution of 4-cyanomethyl-2-cyclopentyloxy-1-methoxybenzene (460 g, 1.99 mol, 1.0 equivalent) in acetonitrile, and methyl acrylate (520 g, 6.0 mol, 3.0 equivalents). The contents of the flask was cooled to −10° C. A pressure equalizing addition funnel was charged with acetonitrile (1.1 L) and benzyltrimethyl ammonium hydroxide (a 40% w/w solution in methanol, 25 g, 0.06 mol, 0.03 equivalents). The contents of the addition funnel was added to the flask. An exotherm was observed, and after stirring for 30 minutes the contents of the flask were cooled to 20° C. The reaction was concentrated under reduced pressure to a residue. To the residue was added toluene (2.6 L). This solution of dimethyl-4-cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)pimelate(90% solution yield) was used directly in the next step.

Workup

  1. customA 12 liter round bottom flask equipped with an overhead stirrer
  2. custominternal thermometer, and a reflux condensor equipped with a nitrogen inlet
  3. customwas flushed with nitrogen
  4. additionaddition funnel
  5. additionThe contents of the addition funnel was added to the flask
  6. temperaturewere cooled to 20° C
  7. concentrationThe reaction was concentrated under reduced pressure to a residue
  8. additionTo the residue was added toluene (2.6 L)

Sources & evidence

ORD record
ord-dfcd962af36d4eee88325866400cc2b9
Source dataset
uspto-grants-2002_01
Patent number
US06337408B1

Reaction notes

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