Water → HCID 86759970, compound

HRID 1795066Notes

Reaction equation

HRID 1795066 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].CC(C)([O-])C.[K+].[CH:18]([Si:21]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[O:22][CH2:23][CH:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)([CH3:20])[CH3:19].O>O1CCCC1>[CH:34]([Si:21]([CH:18]([CH3:20])[CH3:19])([CH:31]([CH3:33])[CH3:32])[O:22][CH2:23][CH:24]1[CH2:29][CH2:28][C:27](=[CH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:26][CH2:25]1)([CH3:35])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 80029Trimethyl phosphonoacetateHCID 22184671HCID 22184671, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86759970HCID 86759970, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6.37 g (35 mmol) of tri methyl phosphonoacetate in 200 mL of tetrahydrofuran (THF) was added 4.28 g (35 mmol) of potassium tert-butoxide. The reaction mixture was stirred at room temperature for 10 minutes. To the resultant slurry was added a solution of 9.3 g (32.7 mmol) of ketone from step C in 20 mL of THF. The mixture was stirred at room temperature under nitrogen overnight, then poured into water and extracted with three 100 mL portions of ether. The combined organic phases were washed sequentially with water, aqueous saturated sodium bicarbonate, and brine, dried over magnesium sulfate, and concentrated to give 10.8 g (97%) of the title compound as a clear oil which was used without further purification. 1H NMR (500 MHz, CDCl3) δ 5.63 (s, 1H), 3.78 (m, 1H), 3.69 (s, 1H), 3.53 (m, 2H), 2.32 (m, 1H), 2.21(m, 1H), 1.97 (m, 2H), 1.76 (m, 1H), 1.10–1.03 (m 23H).

Workup

  1. stirringThe mixture was stirred at room temperature under nitrogen overnight
  2. extractionextracted with three 100 mL portions of ether
  3. washThe combined organic phases were washed sequentially with water, aqueous saturated sodium bicarbonate, and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e151ca222f3c4d2d9fe3e37a1f153c6b
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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