Triethylamine → HCID 86647488, compound

HRID 1808303Notes

Reaction equation

HRID 1808303 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[CH:9]=O)[CH2:2][CH2:3][CH3:4].[Cl-].[CH3:16][O:17][CH:18]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]([O:21][CH3:22])=[O:20].C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:9]=[C:18](\[O:17][CH3:16])/[C:19]([O:21][CH3:22])=[O:20])[CH:11]=[CH:12][C:13]=1[OH:14])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11429511HCID 11429511, compoundHCID 19261375HCID 19261375, compound

Product 1

HCID 86647488HCID 86647488, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

4.0 g (20.6 mmol) of 3-butoxy-4-hydroxybenzaldehyde and 13.25 g (30.9 mmol) of (methoxy(methoxycarbonyl)methyl)triphenylphosphonium chloride are suspended in 40 ml of tetrahydrofuran. 6 ml (42 mmol) of triethylamine are added and then the reaction medium is stirred at 40° C. for 16 hours. The reaction medium is filtered and then the solvents are evaporated. 50 ml of diethyl ether are added and the mixture is stirred at ambient temperature for 10 minutes and then filtered. After evaporation of the solvents, the residue is taken up in a heptane/ethyl acetate 8/2 mixture and then filtered through a silica patch (2 cm). 5.3 g of methyl (Z)-3-(3-butoxy-4-hydroxyphenyl)-2-methoxyacrylate are obtained after evaporation of the solvents.

Workup

  1. filtrationThe reaction medium is filtered
  2. customthe solvents are evaporated
  3. addition50 ml of diethyl ether are added
  4. stirringthe mixture is stirred at ambient temperature for 10 minutes
  5. filtrationfiltered
  6. customAfter evaporation of the solvents
  7. filtrationfiltered through a silica patch (2 cm)

Sources & evidence

ORD record
ord-060def5dc783482cbe836a79af49b696
Source dataset
uspto-grants-2013_01
Patent number
US08357819B2

Reaction notes

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