Water → HCID 23726640, compound

HRID 884377Notes

Reaction equation

HRID 884377 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]=[CH2:14])[C@H:9]1[CH2:15][O:16][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]=[CH2:14])[C@H:9]1[CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 23726637HCID 23726637, compound

Product 1

HCID 23726640HCID 23726640, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.67 g of 163 (5.73 mmol) was dissolved in 35 ml of anhydrous THF, cooled to 0° C. and added with 8.60 ml of TBAF solution (8.60 mmol, 1.5 eq., 1 M/THF). After reacting at RT overnight, 0.5 ml of water was added, followed by stirring for 30 min. Thereafter, the batch was filtered together with a small amount of MTBE over a small amount of silica gel and concentrated. Column chromatography over silica gel (EE/CH 1:3) afforded 1.28 g of alcohol 165 (5.63 mmol, 98%) as a colorless oil.

Workup

  1. filtrationThereafter, the batch was filtered together with a small amount of MTBE over a small amount of silica gel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f572c0baee2042c88cf42ea0784e72f6
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

Loading…