Hydrochloric Acid → HCID 23353039, compound

HRID 233470Notes

Reaction equation

HRID 233470 reaction equation
CC(C)([O-])C.[K+].[P:7]([O-:24])([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:25](Br)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].Cl>CN(C=O)C.C1COCC1>[CH2:36]([P:7]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:24])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 89191-BromododecaneHCID 21904359DibenzylphosphiteHCID 23665647Potassium tert-butoxide

Product 1

HCID 23353039HCID 23353039, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of potassium t-butoxide (6.16 g, 55 mmol), in dry DMF (50 mL), under an argon atmosphere was added dropwise via syringe a solution of dibenzyl phosphite (13.1 g, 50 mmol) in dry DMF (5 mL), and the reaction mixture was stirred at room temperature for 20 min. Then a solution of lauryl bromide (18.6 g, 75 mmol) in dry THF (15 mL), was added dropwise under argon atmosphere, and the mixture was stirred at room temperature for an additional 1 h. After completion of the reaction, the mixture was neutralized with dilute HCl (40 mL) and extracted with ethyl acetate (200 mL), the organic phase was dried, concentrated, and purified by flash chromatography to afford the pure dibenzyl phosphate 14 as a colorless oil (Rf 0.46, silica, ethyl acetate and hexane, 1:2, 10.5 g, 50%).

Workup

  1. stirringthe mixture was stirred at room temperature for an additional 1 h
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (200 mL)
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-cb5b9389d24c450b96caa962ca7d70b0
Source dataset
uspto-grants-1997_01
Patent number
US05593969

Reaction notes

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