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

HRID 964458

Reaction equation

HRID 964458 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-12ae317766c64999bd88ae188a0b1199
Source dataset
uspto-grants-1998_06
Patent number
US05767310

Linked notes

Loading…