Water → HCID 14233170, compound

HRID 1761732Notes

Reaction equation

HRID 1761732 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([O:27][CH:28]([CH3:52])[CH:29]([OH:51])[CH2:30][O:31]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CN(C)C=O>[CH2:11]([O:27][CH:28]([CH3:52])[CH:29]([O:51][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:30][OH:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 142331663-(Hexadecyloxy)-1-(triphenylmethoxy)-2-butanol

Product 1

HCID 14233170HCID 14233170, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5.01 g of 50% sodium hydride in 100 ml of dimethylformamide containing 15.79 g of benzyl bromide at 0° C., was added 46 g of 3-(hexadecyloxy)-1-(triphenylmethoxy)-2-butanol in 50 ml of dimethylformamide. This mixture was stirred overnight at room temperature then poured into water and extracted with petroleum ether. The organic extract was dried and the solvent removed. The residue was dissolved in a mixture of 190 ml of methanol and 100 ml of tetrahydrofuran, then 400 mg of p-toluenesulfonic acid was added. This mixture was allowed to stand overnight, then the solvent was removed. The residue was dissolved in petroleum ether, washed wtih saturated aqueous sodium bicarbonate, dried and the solvent removed, giving and oil. This oil was purified by HPLC using the system hexane:ethyl acetate (9:1), giving 21.84 g of the desired compound as an oil.

Workup

  1. extractionextracted with petroleum ether
  2. extractionThe organic extract
  3. customwas dried
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in a mixture of 190 ml of methanol and 100 ml of tetrahydrofuran
  6. addition400 mg of p-toluenesulfonic acid was added
  7. waitto stand overnight
  8. customthe solvent was removed
  9. dissolutionThe residue was dissolved in petroleum ether
  10. washwashed wtih saturated aqueous sodium bicarbonate
  11. customdried
  12. customthe solvent removed
  13. customgiving
  14. customThis oil was purified by HPLC

Sources & evidence

ORD record
ord-767dcbcfa3b14c269a1ee108b38f649b
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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