2-(T-Butyldimethylsilyloxy)-4-bromoanisole → 5-{[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-hydroxy-methyl}-2-chloro-benzenesulfonamide

HRID 1515436노트

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HRID 1515436 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:15]=1)[O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].C([Li])(C)(C)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26][C:25]=1[S:32]([NH2:35])(=[O:34])=[O:33]>O1CCCC1>[C:11]([Si:8]([CH3:10])([CH3:9])[O:7][C:6]1[CH:15]=[C:2]([CH:30]([OH:31])[C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[C:25]([S:32]([NH2:35])(=[O:33])=[O:34])[CH:26]=2)[CH:3]=[CH:4][C:5]=1[O:16][CH3:17])([CH3:14])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 109800492-(T-Butyldimethylsilyloxy)-4-bromoanisoleHCID 146546022-Chloro-5-formylbenzene-1-sulfonamideHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 581074595-{[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-hydroxy-methyl}-2-chloro-benzenesulfonamide수율 59%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of (5-bromo-2-methoxy-phenoxy)-tert-butyl-dimethyl-silane (2 g, 6.32 mmol) dissolved in tetrahydrofuran (25 mL) at −78° C. under nitrogen is dropwisely added 1.7 M of tert-butyllithium (8.06 mL, 12.6 mmol). The reaction mixture is stirred at −78° C. for 5 minutes. Then, the solution of 2-chloro-5-formyl-benzenesulfonamide (0.462 g, 2.11 mmol) in tetrahydrofuran (5 mL) is added slowly. The reaction mixture is warmed up to room temperature and stirred for 24 h. The reaction is quenched with 1 N of HCl, and extracted with ethyl acetate three times. The combined organic extracts are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (50% ethyl acetate-hexane) provides 0.57 g (59%) of the title compound as a brown oil. 1H NMR (CDCl3): δ 8.00 (m, 1H), 7.40 (m, 2H), 6.70 (d, 3H), 5.70 (s, 1H), 5.00 (m, 2H), 3.70 (s, 3H), 0.90 (s, 9H), 0.05 (s, 6H).

후처리

  1. temperatureThe reaction mixture is warmed up to room temperature
  2. stirringstirred for 24 h
  3. customThe reaction is quenched with 1 N of HCl
  4. extractionextracted with ethyl acetate three times
  5. washThe combined organic extracts are washed with a saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography (50% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-2caf49c3445046d8b117af4bdfdf6b81
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222424B2

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