Diisopropylamine → HCID 22355126, compound

HRID 1769065Notes

Reaction equation

HRID 1769065 reaction equation
[C:1]1([P:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:22]([N-]C(C)C)([CH3:24])[CH3:23].[Li+].C(NC(C)C)(C)C.C([O-])([O-])=[O:38].[K+].[K+]>C1COCC1.O.CC(C)=O.CCOCC>[C:1]1([P:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:9]([C:22]([CH3:24])([CH3:23])[OH:38])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 7912DiisopropylamineHCID 11430Potassium CarbonateHCID 209842Phosphine oxide, (diethoxymethyl)diphenyl-HCID 2724682Lithium diisopropylamide

Product 1

HCID 22355126HCID 22355126, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1-(diphenylphosphinyl)-1,1-diethoxymethane (20 g) in THF (600 mL)/ether (200 mL) at -95° C. was added lithium diisopropylamide (prepared from diisopropylamine (11.5 mL) and nBuLl (7.8 mL, 0.0788 mol), followed by acetone (9.6 mL). The mixture was stirred for 30 minutes, water (100 mL) was added and then after warming the mixture to room temperature K2CO3 was added (4 g). The mixture was extracted with ethyl acetate (2×200 mL), the combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel eluting with ethyl acetate/0.5% triethylamine to afford 1-(diphenylphosphinyl) -1-(1,1-dimethyl-1-hydroxymethyl)-1,1-diethoxymethane.

Workup

  1. additionwas added (4 g)
  2. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate/0.5% triethylamine

Sources & evidence

ORD record
ord-466c36540b564388a06520c1069a83d7
Source dataset
uspto-grants-1995_01
Patent number
US05380729

Reaction notes

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