1,3-Propanediol → HCID 22174480, compound

HRID 1797290Notes

Reaction equation

HRID 1797290 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][O:5][CH2:6][CH2:7]OCCO.[H-].[Na+].C(O)C[CH2:20][OH:21].BrC1C=CC=CC=1CBr>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][CH2:20][OH:21]

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromideHCID 9965373HCID 9965373, compound

Product 1

HCID 22174480HCID 22174480, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The reaction and work up was conducted as described in the preparation of compound 415. Starting materials were NaH (60% in oil, 0.86 g, 22 mmol) in THF (80 mL), 1,3-propanediol (8.67 mL, 120 mmol), 2-bromobenzylbromide (5.0 g, 20 mmol) dissolved in 4 mL dry THF and tetrabutylammonium iodide (0.07 g, 0.2 mmol). The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:1->2:1 as the eluent to afford the title compound as a pale yellow oil.

Workup

  1. customThe reaction and work
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ff92c76aa6c549528883310b9552f661
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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