반응 #601202

반응 방정식

(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)acetate

(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)acetic acid

NBS

AIBN

DCM

→

desired product

(S)-2-tert-Butoxy-2-(1-(4-chlorophenyl)-3-(dimethylaminomethyl) naphthalen-2-yl)acetic acid

용매

CCl4

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed for 5 h
2. 2
   세척washed with sat. NaHCO3
3. 3
   추출extracted with DCM
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타purified by flash column chromatography (silica gel, ethyl acetate/hexanes)

실험 절차

Preparation of(S)-ethyl 2-(3-(bromomethyl)-1-(4-chlorophenyl)naphthalen-2-yl)-2-tert-butoxyacetate: To a solution of (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)acetate (3K, 43 mg, 0.0105 mmol) in CCl4 (2 mL) was added NBS (24 mg, 0.13 mmol) and AIBN (cat. amount). The reaction mixture was refluxed for 5 h. After cooling to room temperature, the reaction mixture was diluted by DCM, washed with sat. NaHCO3, extracted with DCM and the organic layers were combined and dried over MgSO4, filtered, concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to provide 12 mg of the desired product. 1H-MNR 400 MHz (CDCl3) δ: 8.01 (s, 1H), 7.77 (d, J=4 Hz, 1H), 7.43-7.15 (m, 7H), 5.11 (d, J=5.2 Hz, 1H), 5.06 (s, 1H), 5.00 (d, J=5.2 Hz, 1H), 4.07-4.02 (m, 2H), 1.20-1.15 (m, 3H), 0.96 (s, 9H).

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