Chlorotriethylsilane → (S)-ethyl 2-(6-bromo-3-methyl-1-(triethylsilyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

HRID 926188노트

반응식

HRID 926188 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[C:7]([C@H:13]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]([CH3:24])=[CH:5]2.C(N(C(C)C)CC)(C)C.Cl[Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37])=[C:7]([C@H:13]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]([CH3:24])=[CH:5]2

참가 물질

5

반응물 3

HCID 13819ChlorotriethylsilaneHCID 81531DiisopropylethylamineHCID 89681727(S)-ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

생성물 1

HCID 89681729(S)-ethyl 2-(6-bromo-3-methyl-1-(triethylsilyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (238 mg, 0.6 mmol) in anhydrous DCM (20 mL) at 0° C. was added diisopropylethylamine (0.21 mL, 1.2 mmol), followed by chlorotriethylsilane (0.12 mL, 0.72 mmol) and the resulting mixture stirred for 1 hour. The reaction was quenched with saturated sodium bicarbonate solution. The mixture was extracted with DCM and organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give the desired compound. 1H NMR (400 MHz, CDCl3): δ 7.82 (m, 2H), 7.42 (m, 1H), 7.08 (s, 1H), 5.98 (s, 1H), 4.19 (m, 2H), 2.43 (s, 3H), 1.21 (s, 9H), 0.98 (t, 9H), 0.83 (m, 6H).

후처리

  1. customThe reaction was quenched with saturated sodium bicarbonate solution
  2. extractionThe mixture was extracted with DCM and organic layer
  3. concentrationwas concentrated
  4. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-ad394e6d03324e51a2c857732fc4c5c9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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