Propargyl alcohol → HCID 86666343, compound

HRID 335067Notes

Reaction equation

HRID 335067 reaction equation
[CH3:1][C:2]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:3]=1[C:4]([P:6]([C:13](=[O:23])[C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[O:5].[CH2:30](O)[C:31]#C.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>>[CH3:22][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[C:14]=1[C:13]([P:6]([CH2:8][C:9]([O:11][CH2:12][C:30]#[CH:31])=[O:10])([C:4](=[O:5])[C:3]1[C:24]([CH3:29])=[CH:25][C:26]([CH3:28])=[CH:27][C:2]=1[CH3:1])=[O:7])=[O:23]

Participants

4

Reactant 3

HCID 7859Propargyl alcoholHCID 9809426Di-n-butyldilauryltinHCID 59218800HCID 59218800, compound

Product 1

HCID 86666343HCID 86666343, compoundYield 55%

Procedure

2.9 g (7 mmol) methyl 2-(bis(2,4,6-trimethylbenzoyl)-phosphinyl)acetate (example 22) is dissolved in a tenfold excess of 2-propyn-1-ol and heated to 90° C. during 12 hours in the presence of 10 mol % dibutyltin dilaurate. Excess 2-propyn-1-ol is distilled off under vacuum and the residual oil purified by preparative column chromatography (silica gel, eluent toluene/ethyl acetate 9:1). 1.7 g (55%) propyn-3-yl 2-[bis(2,4,6-trimethylbenzoyl)-phosphoryl]acetate are obtained as yellowish oil.

Workup

  1. distillationExcess 2-propyn-1-ol is distilled off under vacuum
  2. customthe residual oil purified by preparative column chromatography (silica gel, eluent toluene/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-aab0b5a5d28b46a095e8d5f7ca003a30
Source dataset
uspto-grants-2014_11
Patent number
US08883872B2

Reaction notes

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