Trimethyl phosphonoacetate → HCID 57705825, compound

HRID 1662322Notes

Reaction equation

[Cl-].[Li+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].N12CCCN=C1CCCCC2.[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

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 (0.76 mL, 5.3 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (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 5.6 (0.45 g, 36%) as a colorless oil.

Workup

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

Sources & evidence

ORD record: ord-fa3ac964d2f7466ab6144c30f03859fe
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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