Water → 2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol

HRID 2075649Notes

Reaction equation

HRID 2075649 reaction equation
[CH2:1]([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]=[C:28]([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(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:27]=[C:26]([O:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH2:75][CH2:76][O:77][CH2:78][CH2:79][O:80][CH2:81][C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.O.C(OCC)(=O)C.C(OCC)(=O)C>C(Cl)Cl.CO>[CH2:1]([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]=[C:28]([CH:27]=[C:26]([O:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH2:75][CH2:76][O:77][CH2:78][CH2:79][O:80][CH2:81][C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH:25]=1)[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][OH:45])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 23514209EtOAc EtOAcHCID 866070451,3-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-5-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene

Product 1

HCID 586877452-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanolYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of Compound 46 (1.22 g, 1.01 mmol) in methylene chloride (15 ml), a methylene chloride solution containing 10% trifluoroacetic acid (7 ml) was added, and water (650 μl) was further added thereto, after which the ice bath was removed, and this was followed by stirring at room temperature for 30 minutes. Triethylamine was poured to the reaction solution, and this was followed by concentration under reduced pressure. The residue obtained was subjected to silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate:methanol 9:1)) to yield Compound 47 (light-yellow oil 977 mg, Y. quant.).

Workup

  1. additionwas added
  2. customafter which the ice bath was removed
  3. additionTriethylamine was poured to the reaction solution
  4. concentrationthis was followed by concentration under reduced pressure
  5. customThe residue obtained

Sources & evidence

ORD record
ord-f49e66adf82f4fa5a44af4373ff31b87
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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