Triethylamine → HCID 86233935, compound

HRID 1359947Notes

Reaction equation

HRID 1359947 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH3:2].C(N([CH2:18][CH3:19])CC)C.[CH:20]([P:22](=[O:27])(OCl)[O:23]Cl)=[CH2:21]>C(Cl)Cl>[CH:20]([P:22]([O:23][C:7]1[CH:6]=[C:5]([CH:10]=[CH:18][CH:19]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:12])([O:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:12])=[O:27])=[CH2:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24522Ethyl 3-hydroxybenzoateHCID 86604306HCID 86604306, compound

Product 1

HCID 86233935HCID 86233935, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution containing ethyl-3-hydroxybenzoate (8 mmol, 1.329 g) and triethylamine (8.3 mmol, 829 mg) in methylene chloride (50 mL) was added dropwise at 0° C. under stirring to a solution of dichloro vinylphosphonate (4 mmol, 0.58 g) in methylene chloride (20 mL). The reaction mixture was stirred at ambient temperature for 24 hours, washed twice with water (40 mL each). The separated organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo to yield 1.61 g (86-99%) of the desired title compound. MS (APPI+): m/e 405 [M+H]+.

Workup

  1. additionwas added dropwise at 0° C.
  2. washwashed twice with water (40 mL each)
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-af92448bd5ff4d7cbf0a8962085038b6
Source dataset
uspto-grants-2011_02
Patent number
US07879826B2

Reaction notes

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