Phytanyl Bromide → HCID 10764965, compound

HRID 2228417Notes

Reaction equation

HRID 2228417 reaction equation
[CH2:1](Br)[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4].[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K]>CN(C=O)C>[CH2:1]([N:26]1[C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]2[C:22]1=[O:32])[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4]

Participants

4

Reactant 2

HCID 10808570Phytanyl BromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 10764965HCID 10764965, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phytanyl bromide (12.34 g), potassium phthalimide (6.95 g) and DMF (50 ml) were heated at 120-130° C. for 4 hours. Most of the DMF was removed under reduced pressure and the crude product was dissolved in dichloromethane (100 ml), washed with water (2×50 ml), dried (MgSO4). The light yellow crude product was chromatographed on flash silica (dichloromethane/hexane as eluant) to yield pure N-phytanyl phthalimide in 11.89 g (80.9%) 1H-n.m.r. (CDCl3) δ0.82-1.8 (m, 39H), 3.73 (t, 2H, CH2N), 7.73 (m, 2H, ArH), 7.88 (m, 2H, ArH); m/z 431 (M+).

Workup

  1. customMost of the DMF was removed under reduced pressure
  2. dissolutionthe crude product was dissolved in dichloromethane (100 ml)
  3. washwashed with water (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. customThe light yellow crude product was chromatographed on flash silica (dichloromethane/hexane as eluant)

Sources & evidence

ORD record
ord-eccd418a86e54286bd5070a68f0d5d73
Source dataset
uspto-grants-2002_07
Patent number
US06417009B1

Reaction notes

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