Water → 2-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)ethanol

HRID 2075634Notes

Reaction equation

HRID 2075634 reaction equation
C([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][C:46](C2C=CC=CC=2)(C2C=CC=CC=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:26][CH:25]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.O.C(OCC)(=O)C>C(Cl)Cl>[CH2:46]([O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][OH:8])=[CH:29][CH:28]=1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 670892521-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]benzene

Product 1

HCID 586877442-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)ethanolYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of Compound 23 (1.43 g, 1.62 mmol) in methylene chloride (20 ml), a methylene chloride solution containing 10% trifluoroacetic acid (10 ml) was added; water (1 ml) was added thereto, after which the ice bath was removed, and this was followed by stirring at room temperature for 2 hours and 30 minutes. The reaction solution was poured over a saturated aqueous solution of sodium hydrogen carbonate to stop the reaction, after which extraction from methylene chloride and chloroform was conducted. The combined organic phases were dried with sodium sulfate, filtered, and concentrated under reduced pressure, after which the residue obtained was subjected to silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate containing 10% methanol)) to yield Compound 24 (light-yellow oil 875 mg, 85%).

Workup

  1. additionwas added
  2. customafter which the ice bath was removed
  3. additionThe reaction solution was poured over a saturated aqueous solution of sodium hydrogen carbonate
  4. customthe reaction
  5. extractionafter which extraction from methylene chloride and chloroform
  6. dry with materialThe combined organic phases were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customafter which the residue obtained

Sources & evidence

ORD record
ord-42cc5d1d08e844d3b1935a7b9c56046e
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

Loading…