Acetic Acid → 4-(2-Trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol

HRID 1727012Notes

Reaction equation

[CH3:1][Si:2]([CH3:24])([CH3:23])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([O:18]C(=O)OC)[CH:9]=1.C[O-].[Na+].CC(O)=O>CO>[CH3:1][Si:2]([CH3:24])([CH3:23])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([OH:18])[CH:9]=1

Participants

Conditions

Temperature: 5 °C

Procedure

5.82 g (16.7 mmol) of carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl ester was dissolved in 100 ml of methanol and cooled down to 5° C.; 3.4 ml=3.30 g (18.4 mmol) of sodium methoxide (5.4 molar in MeOH) was added and the reaction mixture then warmed up to room temperature. After one hour, it was poured into crashed ice, the pH was adjusted to 5-6 with AcOH (1N) and the reaction mixture subsequently extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of n-heptane/MeCl2) to give 4.23 g of 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol as light brown oil.

Workup

temperaturethe reaction mixture then warmed up to room temperature
additionit was poured
extractionthe reaction mixture subsequently extracted twice with MeCl2
washthe organic phases were washed with water
dry with materialdried (MgSO4)
customevaporated
customThe crude product was purified by flash chromatography (SiO2, gradient of n-heptane/MeCl2)

Sources & evidence

ORD record: ord-d140dabd083f4b2cba9d2a6f344b024e
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495001B2

Reaction notes

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