Tetrabutylammonium Fluoride → 2-Hydroxy-5-morpholin-4-yl-benzoic acid methyl ester

HRID 349684Notes

Reaction equation

HRID 349684 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[O:16][Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH:7]=[CH:6][C:5]=1[OH:16]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 692968702-(Tert-butyl-dimethyl-silanyloxy)-5-morpholin-4-yl-benzoic acid methyl ester

Product 1

HCID 588051472-Hydroxy-5-morpholin-4-yl-benzoic acid methyl esterYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(tert-butyl-dimethyl-silanyloxy)-5-morpholin-4-yl-benzoic acid methyl ester (1.0 g, 2.8 mmol) in tetrahydrofuran (35 mL) was treated with tetrabutylammonium fluoride (3.55 g, 11.25 mmol) and stirred for 2 h at room temperature. The reaction mixture was concentrated and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 80/20 hexanes/EtOAc) to yield the final product as a yellow solid (206 mg, 31%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 80/20 hexanes/EtOAc)

Sources & evidence

ORD record
ord-2b933ec33eaf453b9f250a3ee136a262
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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