Water → HCID 58250153, compound

HRID 1045081Notes

Reaction equation

HRID 1045081 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]([S:57]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)(=[O:59])=[O:58])[CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:48]\[CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])(C)(C)C.O>C1COCC1>[C:60]1([S:57]([CH:36]([CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:48]\[CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][OH:24])(=[O:58])=[O:59])[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 58250163HCID 58250163, compound

Product 1

HCID 58250153HCID 58250153, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1 M solution in THF, 0.764 mL, 0.764 mmol) was added drop wise to a stirred solution of tert-butyldiphenyl((17Z,20Z,23Z,26Z)-12-(phenylsulfonyl)dotriaconta-17,20,23,26-tetra-enyloxy)silane (0.16 g, 0.191 mmol) in dry THF (2 mL) and stirring was continued for 1 h. Upon completion of reaction as judged y TLC, water (3 mL) was added and the reaction mixture was extracted with ethyl acetate (3×15 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude was purified by silica gel column chromatography using 30% ethyl acetate/hexane to afford the title product as a clear oil (0.075 g, 66%). 1H NMR (CDCl3): δ7.88 (d, 2H, J=7.2 Hz), 7.57 (m, 3H), 5.38 (m, 8H), 3.65 (br s, 2H), 2.81 (m, 7H), 2.05 (m, 4H), 1.81 (m, 2H), 1.37-1.20 (m, 30H), 1.04 (t, 3H, J=6.9 Hz). m/z (APCI) 599.45 (M++1).

Workup

  1. customUpon completion of reaction
  2. additionwas added
  3. extractionthe reaction mixture was extracted with ethyl acetate (3×15 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e254c83a39324f919d2612c67e6258b0
Source dataset
uspto-grants-2013_10
Patent number
US08563760B2

Reaction notes

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