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Triethylamine → HCID 89614204, compound

HRID 578611
Notes
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Reaction equation

HRID 578611 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5]([CH2:7]Cl)=[CH2:6])[CH3:2].[CH2:10]([O:12][P:13]([CH2:18][CH:19]([CH2:29][OH:30])[CH2:20][P:21](=[O:28])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])(=[O:17])[O:14][CH2:15][CH3:16])[CH3:11].C(N(CC)CC)C>C1COCC1>[CH2:23]([O:22][P:21]([CH2:20][CH:19]([CH2:29][O:30][CH2:7][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:9])=[CH2:6])[CH2:18][P:13](=[O:17])([O:14][CH2:15][CH3:16])[O:12][CH2:10][CH3:11])(=[O:28])[O:25][CH2:26][CH3:27])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11073578Ethyl 2-(Chloromethyl)acrylate (stabilized with HQ)HCID 11759759HCID 11759759, compound

Product 1

HCID 89614204HCID 89614204, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl-2-(chloromethyl)-acrylate (3.86 g, 26.0 mmol, 1.5 eq.) was added to a solution of 2-hydroxymethyl-1,3-propylene-bisphosphonic acid tetraethylester (6.0 g, 17.3 mmol) and triethylamine (3.62 ml, 26 mmol, 1.5 eq.) in anhydrous THF (30 ml), and the reaction mixture was stirred for 45 h at 70° C. After concentrating in vacuo deionized water (50 ml) was added and the obtained solution was extracted with ethylacetate (3×50 ml). The combined organic phases were dried with anhydrous sodium sulphate. After removal of the solvent under reduced pressure the obtained crude product was purified by column chromatography (eluent: ethylacetate/methanol 98:2). 3.77 g (48% yield) of the product was obtained as a yellowish oil.

Workup

  1. concentrationAfter concentrating in vacuo deionized water (50 ml)
  2. additionwas added
  3. extractionthe obtained solution was extracted with ethylacetate (3×50 ml)
  4. dry with materialThe combined organic phases were dried with anhydrous sodium sulphate
  5. customAfter removal of the solvent under reduced pressure the
  6. customobtained crude product
  7. customwas purified by column chromatography (eluent: ethylacetate/methanol 98:2)

Sources & evidence

ORD record
ord-84f9ab5e258a4a0c97e0075199b343f1
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040602B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes