Triethylamine → HCID 59172010, compound

HRID 1952417Notes

Reaction equation

HRID 1952417 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].C(N(CC)CC)C.[Br:28][C:29]([CH3:34])([CH3:33])[C:30](Br)=[O:31]>C(Cl)Cl.C(OCC)(=O)C>[CH2:18]([O:17][P:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:30](=[O:31])[C:29]([Br:28])([CH3:34])[CH3:33])([O:14][CH2:15][CH3:16])=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromideHCID 45158972Diethyl (11-hydroxyundecyl)phosphonate

Product 1

HCID 59172010HCID 59172010, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Diethyl 11-hydroxyundecylphosphonate (1.00 g, 3.24 mmol) and triethylamine (0.328 g, 3.24 mmol) were dissolved in ˜20 mL dry DCM in a 50 mL rbf under argon. This mixture was stirred and put in an ice bath. Bromo-isobutyryl bromide (0.719 g, 3.56 mmol) was added dropwise via syringe. After 3.5 hours a thin layer chromatogram (tlc) was taken in ethyl acetate. A column was run in ethyl acetate and the after removal of the solvent the desired compound was obtained as an orange oil (1.050 g, 75% yield). Analysis found (calculated) %: C, 47.56 (47.65); H, 7.98 (7.86).

Workup

  1. customput in an ice bath
  2. customthe after removal of the solvent the desired compound

Sources & evidence

ORD record
ord-447b568f563d41f5b81151be31f7d6bd
Source dataset
uspto-grants-2013_03
Patent number
US08405069B2

Reaction notes

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