Water → HCID 23043525, compound

HRID 2165063Notes

Reaction equation

HRID 2165063 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.COC1C=CC(C(C2C=CC=CC=2)(C2C=CC=CC=2)[O:20][CH2:21][CH:22]([OH:41])[CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH3:40])=CC=1.O>CN(C)C=O>[C:4]1([CH2:3][O:41][CH:22]([CH2:21][OH:20])[CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH3:40])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23043527HCID 23043527, compound

Product 1

HCID 23043525HCID 23043525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 3.26 g of unwashed 50% sodium hydride and 10.9 g of benzyl bromide in 40 ml of dimethylformamide, under argon, was added a solution of 27.14 g of 20-[(4-methoxyphenyl)diphenylmethoxy]-2,5,8,17-tetraoxaeicosan-19-ol in 50 ml of dimethylformamide over 1/2 hour. This mixture was stirred overnight, water was then added and the mixture extracted with ether. The ether extract was washed with water, dried and the solvent removed. The residue was dissolved in hot methanol and stirred with 10 g of a strongly acidic ion exchange resin. This mixture was filtered and the solvent removed. The residue was purified by HPLC, eluting with hexane:ethyl acetate (65:35) giving the desired compound as 12.9 g of a light yellow oil.

Workup

  1. extractionthe mixture extracted with ether
  2. extractionThe ether extract
  3. washwas washed with water
  4. customdried
  5. customthe solvent removed
  6. dissolutionThe residue was dissolved in hot methanol
  7. stirringstirred with 10 g of a strongly acidic ion exchange resin
  8. filtrationThis mixture was filtered
  9. customthe solvent removed
  10. customThe residue was purified by HPLC
  11. washeluting with hexane:ethyl acetate (65:35)

Sources & evidence

ORD record
ord-6b09bca02c6b4cc0a2d49d76f58de2dd
Source dataset
uspto-grants-1990_07
Patent number
US04939127

Reaction notes

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