1,1,3,3-Tetramethylguanidine → HCID 57925910, compound

HRID 1013463Notes

Reaction equation

HRID 1013463 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[CH3:13][C:14]1([CH3:21])[CH2:19][O:18][PH:17](=[O:20])[O:16][CH2:15]1.CN(C)C(N(C)C)=N>C1(C)C=CC=CC=1.Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][P:17]2(=[O:20])[O:18][CH2:19][C:14]([CH3:21])([CH3:13])[CH2:15][O:16]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 777171,3,2-Dioxaphosphorinane, 5,5-dimethyl-, 2-oxideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 57925910HCID 57925910, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Procedure

4-Bromomethyl-benzoic acid methyl ester (0.50 g, 2.18 mmol) was made 2.0 M in anhydrous toluene and to this mixture was added 5,5-dimethyl-[1,3,2]dioxaphosphinane 2-oxide (0.66 g, 4.37 mmol) followed by N,N,N′,N′-tetramethyl-guanidine (0.25 g, 2.18 mmol). The mixture was stirred at ambient temperature for 18 hours. The reaction mixture was then diluted with 1N aq HCl and extracted with EtOAc. The organic layer was again washed with 1 N aqueous HCl, brine, dried (MgSO4) then concentrated in vacuo. The residue was purified by MPLC (0-70% EtOAc in CH2Cl2) to afford the title compound: MS: cal'd 299 (MH+), exp 299 (MH+)

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was again washed with 1 N aqueous HCl, brine
  3. dry with materialdried (MgSO4)
  4. concentrationthen concentrated in vacuo
  5. customThe residue was purified by MPLC (0-70% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-259ed4bfbc024b128f29dcd5b08dc25c
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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