Ethanol → HCID 19922567, compound

HRID 1647968Notes

Reaction equation

HRID 1647968 reaction equation
[C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[C:21]([P:26](=[O:29])([OH:28])[OH:27])[P:22](=[O:25])([OH:24])[OH:23])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[O-]CC.[Na+:33].C(O)C>O1CCCC1>[C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[C:21]([P:26](=[O:27])([O-:28])[O-:29])[P:22](=[O:23])([O-:24])[O-: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].[Na+:33].[Na+:33].[Na+:33].[Na+:33]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 19033956HCID 19033956, compound

Product 1

HCID 19922567HCID 19922567, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[2-[2-(1-Tridecynyl)phenyl]ethenylidene]bisphosphonic acid (0.102 g, 0.23 mmol) prepared according to Example 10 was dissolved in dry tetrahydrofuran (10 ml) and stirred while sodium ethoxide in ethanol (0,177M, 5.19 ml, 0.92 mmol) was added. After 20 minutes, the solvent was removed under reduced pressure to give a light solid. The solid was powdered and washed with dry ethanol, then dried under vacuum, 40.8 mg, 0.084 mmol, 36.5% yield; mp darkens above 233° C. under N2 ; 1H NMR (D2O) ∂ 0.89 (m, 3H), 1.21 to 1.57 (m, 16H), 1.67 (m, 2H), 2.55 (t, J=7.1 Hz, 2H), 7.35 (m, 2H), 7.51 (m, 1H), 7.90 (dd, J=42.4, 26.3 Hz, 1H), 8.19 (d, J=7.7 Hz, 1H).

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customto give a light solid
  4. washwashed with dry ethanol
  5. customdried under vacuum, 40.8 mg, 0.084 mmol, 36.5% yield
  6. custommp darkens above 233° C.

Sources & evidence

ORD record
ord-0ea83981103c4d10bb33ffabacdfa4c1
Source dataset
uspto-grants-1995_07
Patent number
US05434288

Reaction notes

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