Reaktion #411786

Reaktionsgleichung

ethyl acetate

compound

3-[4-hydroxy-3-methylphenyl)-3-[3-methyl-4-(2-hydroxy-3,3-dimethylbutoxy)phenyl]pentane

NaH

ethyl acetate

pinacolone

→

11

Ausbeute 92.3%

3-[3-methyl-4(2-hydroxy-3,3-dimethylbutoxy)phenyl]-3-[3-methyl-4-(3,3-dimethyl-2-oxobutoxy)phenyl]pentane

Ausbeute 92.3%

Lösungsmittel

DMF

—

hexanes

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred at ambient temperature for I
2. 2
   SonstigeThe reaction mixture was quenched with water
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   SonstigeThe organic fraction was separated
5. 5
   Waschenwashed with water and brine
6. 6
   Trocknendried over MgSO4
7. 7
   Einengenconcentrated in vacuo

Vorschrift

To a solution of the compound of example 7 (100 mg, 0.26 mmol) in DMF (2.5 mL) was added NaH (7.0 mg, 0.29 mmol). The reaction mixture was stirred at ambient temperature for 30 min, then pinacolone (39 mg, 0.29 mmol) was added. The reaction was stirred at ambient temperature for I h or until judged complete by TLC (20% ethyl acetate in hexanes). The reaction mixture was quenched with water, and diluted with ethyl acetate. The organic fraction was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 10% ethyl acetate in hexanes) afforded 117 mg (0.24 mmol, 92%) of 11. 1HNMR (CDCl3) δ: 6.91 (m, 4 H, Ar—H), 6.69 (d, J=8.3 Hz, 1 H, Ar—H), 6.49 (d, J=8.3 Hz, 1 H, Ar—H), 4.83 (s, 2 H, CH2), 4.09 (dd, J=11.3 Hz, J=3.3 Hz, 1 H, CH2), 3.85 (t, J=11.3 Hz, 1 H, CH2), 3.69 (d, J=11.3 Hz, 1 H, CH2), 2.23 (s, 3 H), Ar—CH3), 2.18 (s, 3 H, Ar—CH3), 2.00 (q, J=7.3 Hz, 4 H, CH2CH3), 1.24 (s, 9 H, t-Bu), 1.00 (s, 9 H, t-Bu), 0.58 (t, J=7.3 Hz, 6 H, CH2CH3).

Quelle