Tetrabutylammonium Fluoride → HCID 86618187, compound

HRID 2380942Notes

Reaction equation

HRID 2380942 reaction equation
[Si]([O:18][CH:19]([CH:57]([CH3:59])[CH3:58])[CH2:20][CH2:21][CH:22]([C:24]1([CH3:56])[CH2:28][CH2:27][CH:26](/[CH:29]=[CH:30]/[CH:31]=[C:32]2[CH2:37][CH:36]([O:38][Si](C(C)(C)C)(C)C)[CH2:35][CH:34]([O:46][Si](C(C)(C)C)(C)C)[CH2:33]2)[C:25]1([CH3:55])[CH3:54])[CH3:23])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:18][C@H:19]([CH:57]([CH3:59])[CH3:58])[CH2:20][CH2:21][C@@H:22]([C:24]1([CH3:56])[CH2:28][CH2:27][C@@H:26](/[CH:29]=[CH:30]/[CH:31]=[C:32]2[CH2:33][C@@H:34]([OH:46])[CH2:35][C@H:36]([OH:38])[CH2:37]2)[C:25]1([CH3:55])[CH3:54])[CH3:23]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 87504715HCID 87504715, compound

Product 1

HCID 86618187HCID 86618187, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of intermediate (21) (0.14 mmol) in THF (4 mL) was added n-Bu4NF (1 M solution in THF; 2.1 mL, 2.1 mmol). The reaction mixture was stirred at room temperature for 12 hours and then loaded onto a silica gel column. The reaction product was eluted (n-pentane/Me2CO) and further purified by HPLC over silica to afford 0.0035 g, (44% yield) of the desired product (22) which was characterized as follows:

Workup

  1. washThe reaction product was eluted (n-pentane/Me2CO)
  2. customfurther purified by HPLC over silica

Sources & evidence

ORD record
ord-b9de8b68d0434fc2a97bf37b182ded37
Source dataset
uspto-grants-2012_09
Patent number
US08258126B2

Reaction notes

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