HCID 57814825, compound → HCID 57845584, compound

HRID 1254168Notes

Reaction equation

HRID 1254168 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][C@@H:12]([Cl:22])[C@@H:11]1[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])(C(C)(C)C)(C)C>CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>[Cl:22][C@H:12]1[C@H:11]([CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[C@@H:10]([CH2:9][OH:8])[C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13]1

Participants

3

Reactant 1

HCID 57814825HCID 57814825, compound

Product 1

HCID 57845584HCID 57845584, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 11078149TBAF tetrahydrofuranSolvent

Procedure

A solution of 1.46 g (2.8 mmol) of silyl ether 3 in 10 mL of 1.0M TBAF/THF was stirred at 25° C. for 3 h. The THF solvent was then removed in vacuo and the residual oil was taken up in ethyl acetate (100 mL) and washed with 2×75 mL of saturated aqueous ammonium chloride, brine, and dried over anhydrous sodium sulfate (50 g). The mixture was then filtered and the filtrate was concentrated in vacuo to yield 1.18 g (quantitative yield) of alcohol 4 used in the next step without purification; 1H NMR (CDCl3): 1.42-1.98 (m, 12H), 2.0-2.48 (m, 8H), 3.45-4.44 (m, 6H), 4.54-4.76 (m, 3H), 5.20-5.55 (m, 4H), 5.91 (m, 1H).

Workup

  1. customThe THF solvent was then removed in vacuo
  2. washwashed with 2×75 mL of saturated aqueous ammonium chloride, brine
  3. dry with materialdried over anhydrous sodium sulfate (50 g)
  4. filtrationThe mixture was then filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4870462c10b44d1eab96e0be6093220f
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

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