1-Methylimidazole → Dimethyl erucyl phosphate

HRID 497005

Reaction equation

HRID 497005 reaction equation
[P:1]([O: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]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([O:5][CH3:6])([O:3][CH3:4])=[O:2].C(O)CCCCCCCCCCC/C=C\CCCCCCCC.CN1C=CN=C1.P(Cl)(OC)(OC)=O>C(Cl)Cl>[P:1]([O-:7])([O:5][CH3:6])([O:3][CH3:4])=[O:2].[P:1]([O: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]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([O:5][CH3:6])([O:3][CH3:4])=[O:2]

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 101863Phosphorochloridic acid, dimethyl esterHCID 5354168Erucyl alcoholHCID 86619244Dimethyl erucyl phosphate2×

Product 2

HCID 3753418Dimethyl phosphate anionHCID 86619244Dimethyl erucyl phosphateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl erucyl phosphate (Compound 70) To a solution of erucyl alcohol (0.50 g, 1.5 mmol) in dry CH2Cl2 (10 mL) was added N-methylimidazole (0.14 mL, 1.7 mmol) followed by the addition of dimethyl chlorophosphate (0.20 mL, 1.9 mmol). After 20 hours, the reaction mixture was concentrated and subjected to silica-gel column chromatography [eluent: hexane/ethyl acetate, 66/33, v/v] to give dimethyl phosphate Compound 70 (0.59 g, 89%) as an oil.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f63ca7fff0c04821a3c9365f8c6e383b
Source dataset
uspto-grants-2005_09
Patent number
US06949528B1

Linked notes

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