Diethanolamine → HCID 10224851, compound

HRID 1797282Notes

Reaction equation

HRID 1797282 reaction equation
C(N(C(C)C)C(C)C)C.[NH:10]([CH2:14][CH2:15][OH:16])[CH2:11][CH2:12][OH:13].Br[CH2:18]/[CH:19]=[CH:20]/[Sn:21]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C>[CH2:30]([Sn:21]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])/[CH:20]=[CH:19]/[CH2:18][N:10]([CH2:14][CH2:15][OH:16])[CH2:11][CH2:12][OH:13])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 81531DiisopropylethylamineHCID 10905679167288-95-1

Product 1

HCID 10224851HCID 10224851, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

N-Ethyl-N,N-diisopropylamine (315 mg) was added to a solution of diethanolamine (256 mg) in dry DMF (5 mL) at 0° C. [(1E)-3-bromoprop-1-enyl](tributyl)stannane (600 mg) was added to the reaction after 10 min. The reaction mixture was stirred for 15 h at 20° C. and then quenched with saturated NH4Cl (aq.). Extraction with Et2O and drying (MgSO4) of the organic phase gave, after concentration in vacuo, the crude product. Purification was done by chromatography eluting with Et2O/MeOH 100:4 to afford the title compound as a liquid.

Workup

  1. additionwas added to the reaction after 10 min
  2. customquenched with saturated NH4Cl (aq.)
  3. extractionExtraction with Et2O
  4. dry with materialdrying (MgSO4) of the organic phase
  5. customgave
  6. concentrationafter concentration in vacuo
  7. customPurification
  8. washeluting with Et2O/MeOH 100:4

Sources & evidence

ORD record
ord-0d3e1ae87f7b4061b142c37b49bf6696
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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