Sodium Iodide → HCID 23716562, compound

HRID 2119773Notes

Reaction equation

HRID 2119773 reaction equation
[CH2:1]([O:21][C:22]([P:24](=[O:29])([O:27]C)[O:25][CH3:26])=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[Na+:30].[I-].CN(C=O)C.[K+].[Br-]>CC(C)=O.C1COCC1>[CH2:1]([O:21][C:22]([P:24](=[O:27])([O-:29])[O:25][CH3:26])=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[Na+:30]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 253877Potassium BromideHCID 10646503Dimethyl 1-eicosanyloxycarbonylphosphonate

Product 1

HCID 23716562HCID 23716562, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Demethylation of dimethyl 1-eicosanyloxycarbonylphosphonate with NaI was carried out as described in Example 8 above except for the solvent, which was a mixture of DMF (3 mL), THF (8 mL), and acetone (2 mL); yield 0.86 g (84%); mp 95-96° C.; IR (KBr): υ 2960, 2930, 2860, 1735, 1470, 1235, 1220 cm−1; 1H NMR (CDCl3+CD2OD) δ0.8-1.8 (m, 39H, CH3(CH2)18), 3.8 (d, 3H, P(ONa)(OCH3)), 4.2 (t, 2H, CH2O). Anal. Calcd. for C22H44O5NaP: C, 59.69; H, 10.04; N, 5.19; P, 7.00. Found: C, 59.94; H, 10.00; Na, 5.19; P, 7.06.

Sources & evidence

ORD record
ord-7a4465518d8042aa94c58ab1d48faed4
Source dataset
uspto-grants-2004_02
Patent number
US06686462B2

Reaction notes

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