Tetrabutylammonium Fluoride → HCID 19380935, compound

HRID 257741Notes

Reaction equation

HRID 257741 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 30 (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 31 (19 g) as a yellow crystalline solid.

Workup

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

Sources & evidence

ORD record
ord-24b23b75733c471893aa21ba58785f54
Source dataset
uspto-grants-1993_11
Patent number
US05264420

Reaction notes

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