Diethyl Ether → HCID 19033961, compound

HRID 265244Notes

Reaction equation

HRID 265244 reaction equation
[C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[C:21](P(=O)(OCC)OCC)[P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH-].[Li+].CCOCC>O1CCCC1.O>[C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1/[CH:20]=[CH:21]/[P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 54279876HCID 54279876, compound

Product 1

HCID 19033961HCID 19033961, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tetraethyl [2-[2-(1-tridecynyl)phenyl]ethenylidene]bisphosphonate (2.0 g, 3.61 mmol) prepared according to Example 9 was dissolved in tetrahydrofuran (26 ml). Lithium hydroxide (0.152 g, 3.62 mmol) was dissolved in water (10 ml) and added to the tetrahydrofuran solution. After stirring the reaction overnight, ether was added, and the aqueous phase was extracted with ether. The combined ether layers were dried (MgSO4) and stripped down. The residue was chromatographed on silica eluting with 3% ethanol in hexane. Tlc on silica, developed in 5% ethanol in hexane, was used to identify product, Rf =0.04. Impure fractions were combined and rechromatographed as necessary to give 1.21 g, 2.89 mmol, 80% yield of the product as a pale yellow liquid; 1H NMR (CDCl3) ∂0.88 (m, 3H), 1.15 to 1.81 (several m, 24H), 2.46 (t, J=7.1 Hz), 4.15 (m, 4H), 6.37 (t, J=18 Hz, 1H), 7.26 (m, 2H), 7.42 (m, 1H), 7.54 (m, 1H), 7.95 (dd, J=23.0, 17.7 Hz, 1H); EI mass spectrum m/z 419 (M+H)+.

Workup

  1. additionwas added
  2. extractionthe aqueous phase was extracted with ether
  3. dry with materialThe combined ether layers were dried (MgSO4)
  4. customThe residue was chromatographed on silica eluting with 3% ethanol in hexane
  5. customrechromatographed as necessary

Sources & evidence

ORD record
ord-9d013e1587a04df08c5807c05785f136
Source dataset
uspto-grants-1997_07
Patent number
US05648349

Reaction notes

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