Tetrabutylammonium Fluoride → HCID 19380935, compound

HRID 1198487Notes

Reaction equation

HRID 1198487 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].C([Si](O[Si](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 mi) 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); 1H NMR (CDCl3) δ 8.42 (m, 1H), 7.55 (d, J=7 Hz, 1H), 7.36 (t, J=7 Hz, 1H), 7.29 (t, J=7 Hz, 1H), 7.27 (7d, J=7 Hz, 1H), 7.22 (s, 1H), 3.76 (t, J= 7 Hz, 2H), 2.82 (t, J=7 Hz, 2H) 2.61 (s, 3H), 2.00 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-b644d4636d7e4e9da3de570f6f65eb28
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

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