Tetrabutylammonium Fluoride → 2,6-Dipropyl-4-(2-hydroxyethyl)phenol

HRID 1378841

Reaction equation

HRID 1378841 reaction equation
[Si]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH2:18][CH2:19][OH:20])=[CH:11][C:10]=1[CH2:21][CH2:22][CH3:23])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:21]([C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][OH:20])[CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:9]=1[OH:8])[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19080442t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene

Product 1

HCID 190803732,6-Dipropyl-4-(2-hydroxyethyl)phenolYield 170.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.0 g (2.98 mmol) of the product of Step C in 3.0 mL of THF was added 3.57 mL (3.57 mmol) of 1.0N solution of tetrabutylammonium fluoride in THF. After 15 minutes TLC indicated that the reaction was complete. The reaction mixture was concentrated and then purified by flash chromatography (silica gel, hexane/ethyl acetate 3:1) to give 1.13 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography (silica gel, hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-2ec0b3648f4e4ce9aa1b431cbce5977c
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Linked notes

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