Diisopropylethylamine → HCID 19359345, compound

HRID 376820Notes

Reaction equation

HRID 376820 reaction equation
[CH:1]([N:4]([CH:7]([CH3:9])[CH3:8])CC)([CH3:3])[CH3:2].Cl[PH:11][O:12][CH2:13]N(C(C)C)C(C)C.[O:21]=[C:22]([CH3:28])[CH2:23][CH2:24][CH2:25][CH2:26][OH:27]>C(Cl)Cl.C(OCC)(=O)C>[CH:7]([N:4]([CH:1]([CH3:2])[CH3:3])[P:11]([O:12][CH3:13])[O:27][CH2:26][CH2:25][CH2:24][CH2:23][C:22](=[O:21])[CH3:28])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 890776-Hydroxyhexan-2-oneHCID 18325664HCID 18325664, compound

Product 1

HCID 19359345HCID 19359345, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a rapidly stirred solution of diisopropylethylamine (2.3 ml, 13 mmol) and chlorodiisopropylaminomethoxyphosphine (1.4 ml, 6.5 mmol) in CH2Cl2 (15 ml) was added dropwise to a solution of 5-oxo-1-hexanol (0.58 g, 5 mmol) in CH2CL2 (7 ml) over 10 min. The reaction was stirred at room temperature for an additional 10 min, diluted with ethyl acetate (100 ml) and extracted with saturated aqueous NaCl (with 5% NaHCO3 5, 3×75 ml). The ethyl acetate layer was dried over MgSO4, filtered, concentrated and distilled in vacuo to yield 0.65 g of the methyl ketone phosphoramidite (50%).

Workup

  1. extractionextracted with saturated aqueous NaCl (with 5% NaHCO3 5, 3×75 ml)
  2. dry with materialThe ethyl acetate layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-c634a35f44304e8488435f62a4e7ed3c
Source dataset
uspto-grants-2000_02
Patent number
US06022714

Reaction notes

Loading…