Diisopropylamine → HCID 57077693, compound

HRID 247812Notes

Reaction equation

HRID 247812 reaction equation
C1([CH:7]([SeH])[CH2:8][O:9][CH2:10][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])C=CC=CC=1.C(=O)(O)[O-].[Na+].I([O-])(=O)(=O)=O.[Na+].C(NC(C)C)(C)C>O1CCOCC1CO.O.C(Cl)Cl.C1C=CC=CC=1>[CH:8]([O:9][CH2:10][P:11]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:18])=[CH2:7]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 131717892HCID 131717892, compound

Product 1

HCID 57077693HCID 57077693, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6344DichloromethaneSolventHCID 69597608HCID 69597608, compoundSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 28 (30 g, 0.081 mol) in dioxane-methanol-water (6:2:1, 600 ml) was added sodium bicarbonate (34 g, 0.4 mol) followed by sodium periodate (51 g, 0.24 mol). After stirring for 30 minutes, the mixture was filtered. The filtrate was condensed to ca 100 ml volume diluted with CH2Cl2 (500 ml) and washed with brine. Evaporation of dried (MgSO4) solvent gave a colorless oil which was dissolved in benzene (200 ml). Diisopropylamine (30 g, 0.3 mol) was added and the solution was heated at 90° C. for 30 minutes. All volatiles were removed in vacuo and the residual oil was chromatographed on silica gel using CH2Cl2 -MeOH (3%) as eluent to give 18 (15.3 g, 95%) as a colorless oil. 1H-NMR (300 MHz CDCl3) δ 1.25 (T, J=7.2Hz, 6H), 3.86 (d, J=9 6Hz, 2H), 4.01-4.15 (m, 5H), 4.20 (dd, J=3.6, 14.7Hz, 1H), 6.42 (dd, J=6.6, 14.7Hz, 1H).

Workup

  1. filtrationthe mixture was filtered
  2. customcondensed to ca 100 ml volume
  3. washwashed with brine
  4. customEvaporation
  5. dry with materialof dried (MgSO4) solvent
  6. customgave a colorless oil which
  7. customAll volatiles were removed in vacuo
  8. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-ea637002dcb7458d87b6db2b2af42e1c
Source dataset
uspto-grants-1993_05
Patent number
US05208221

Reaction notes

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