Ethanol → HCID 86748801, compound

HRID 265239Notes

Reaction equation

HRID 265239 reaction equation
[C:1]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([P:26](=[O:29])([OH:28])[OH:27])[P:22](=[O:25])([OH:24])[OH:23])[CH:17]=[CH:18][CH:19]=1)#[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:15]=[C:16]([CH:20]=[C:21]([P:26](=[O:27])([O-:28])[O-:29])[P:22](=[O:23])([OH:24])[OH:25])[CH:17]=[CH:18][CH:19]=1)#[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]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 19033968HCID 19033968, compound

Product 1

HCID 86748801HCID 86748801, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[2-[3-(1-Tridecynyl)phenyl]ethenylidene]bisphosphonic acid (0.103 g, 0.223 mmol) prepared according to Example 2 was dissolved in dry tetrahydrofuran (10 ml) and stirred while sodium ethoxide in ethanol (0.177M, 2.58 ml, 0.457 mmol) was added. After one hour, the solvent was removed under reduced pressure leaving a brownish yellow solid. This solid was powdered and washed successively with anhydrous ether, tetrahydrofuran, acetonitrile, and ethanol leaving a white solid, 43.3 mg, 0.089 mmol, 38% yield; 1H NMR (D2O, relative to HOD peak at 4.64) ∂0.76 (t, J=6.9 Hz, 3H), 1.05 to 1.58 (several m, 18H), 2.35 (t, J=7.0 Hz, 2H), 7.30 (m, 2H), 7.55 (dd, J=43.8, 27.0 Hz, 1H), 7.69 (m, 2H); FAB mass spectrum m/z 443 (M-2Na+3H)+, 465 (M-Na+2H)+, 487 (M+H)+.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customleaving a brownish yellow solid
  4. washwashed successively with anhydrous ether, tetrahydrofuran, acetonitrile, and ethanol leaving a white solid, 43.3 mg, 0.089 mmol, 38% yield

Sources & evidence

ORD record
ord-0eae36aa491a44c08fa958fe2b87e469
Source dataset
uspto-grants-1997_07
Patent number
US05648349

Reaction notes

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