Ammonium Chloride → Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]-3-methylbutanoate

HRID 1690624Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:24]([CH3:32])([CH3:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:10]=[CH:11][C:12]=1[O:13][Si](C(C)C)(C(C)C)C(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[OH:13][C:12]1[CH:11]=[CH:10][C:9]([C:24]([CH3:32])([CH3:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:8][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

In a round bottom flask, was introduced ethyl 3-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}-3-methylbutanoate (2.60 g, 5.6 mmol) and tetrahydrofuran (18 mL). The mixture was cooled to 0° C. and tetrabutylammonium fluoride (1N in THF, 8.4 mL) was added. The solution was stirred for 2 hrs and hydrolyzed with saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 1.7 g (99%) of the desired product as a yellow oil.

Workup

extractionThe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2)

Sources & evidence

ORD record: ord-9bdd596a6fc6461c9717e41af3409bac
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153647B2

Reaction notes

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