Trimethyl phosphonoacetate → HCID 57705825, compound

HRID 1662352Notes

Reaction equation

HRID 1662352 reaction equation
[Cl-].[Li+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].C1CCN2C(=NCCC2)CC1.[CH3:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:29]=1)=O>CC#N.CCOC(C)=O>[C:36]1([CH2:35][O:34][C:30]2[CH:29]=[C:28](/[C:26](/[CH3:25])=[CH:7]/[C:5]([O:4][CH3:3])=[O:6])[CH:33]=[CH:32][CH:31]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 80029Trimethyl phosphonoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-oneHCID 433294Lithium Chloride

Product 1

HCID 57705825HCID 57705825, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of lithium chloride (0.28 g, 6.6 mmol) in MeCN (9 mL), were added trimethyl phosphonoacetate (available from Aldrich) (0.76 mL, 5.3 mmol), DBU (0.79 mL, 5.3 mmol), and 3-benzyloxyacetophenone (available from Aldrich) (1.00 g, 4.4 mmol). The mixture was stirred overnight at reflux (100° C.), cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The crude product was chromatographed on silica gel (0-10% EtOAc/hexane) to afford 42.1 (0.45 g, 36%) as a colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel (0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-8367a32484fb4be9a4c18a81ea8b29d7
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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