Tetrabutylammonium Fluoride → HCID 19380935, compound

HRID 1109506Notes

Reaction equation

HRID 1109506 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:5]1)(=[O:3])[CH3:2].[Si](O[Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOCC.CC(O)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70043507HCID 70043507, compound

Product 1

HCID 19380935HCID 19380935, compoundYield 108%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the silyl ether 3 (27 g, 81 mmol) in THF (270 mL) at ambient temperature was added a premixed solution of n-Bu4NF (1M in THF: 244 mL, 0.24 mol) and AcOH (14 mL, 0.24 mmol) (1:1). After 20 hours the reaction mixture was diluted with ether and then washed with H2O (2 times) and brine, dried (MgSO4), and concentrated to give the alcohol 4 (19 g) as a yellow crystalline solid. TLC Rf=0.35 (60% ethyl acetate/hexanes);

Workup

  1. washwashed with H2O (2 times) and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-251cfe64c305444f999d20c3f4a52c4b
Source dataset
uspto-grants-1994_06
Patent number
US05321034

Reaction notes

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