p-Toluidine → N-(4-Methylphenyl)-1,1-dimethyl-1-(2-methyl-1H-inden-7-yl)silanamine

HRID 557498노트

반응식

HRID 557498 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Li]CCCC.Cl[Si:15]([CH3:27])([CH3:26])[C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:24]=1[CH2:23][C:22]([CH3:25])=[CH:21]2>C1COCC1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][Si:15]([CH3:26])([CH3:27])[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:24]=2[CH2:23][C:22]([CH3:25])=[CH:21]3)=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 7813p-ToluidineHCID 58418828chloro(dimethyl)(2-methyl-1H-inden-7-yl)silaneHCID 178418339Butyllithium

생성물 1

HCID 58418709N-(4-Methylphenyl)-1,1-dimethyl-1-(2-methyl-1H-inden-7-yl)silanamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 6.44 g (60.0 mmol) of p-toluidine in 180 mL of THF 24.0 mL (60.0 mmol) of 2.5 M nBuLi in hexanes was added at 0° C. This mixture was additionally stirred for 4 hours at room temperature, then cooled to −40° C., and a solution of 13.4 g (60.0 mmol) of chloro(dimethyl)(2-methyl-1H-inden-7-yl)silane in 50 mL of THF was added in one portion. The resulting mixture was stirred for 12 hours at room temperature and then evaporated to dryness. To the residue 100 mL of ether was added, and the obtained suspension was stirred for 20 minutes, and then filtered through glass frit (G3). The precipitate was additionally washed with 2×100 mL of ether. The combined filtrate was evaporated to dryness, and the residue was washed with 2×15 mL of cold hexanes and then dried in vacuum. Yield 11.3 g (64%) of white solid. 1H NMR (CD2Cl2): δ 7.40 (dd, J=7.3 Hz, J=1.3 Hz, 1H, 6-H in indenyl), 7.32 (dd, J=7.3 Hz, J=1.3 Hz, 1H, 4-H in indenyl), 7.26 (t, J=7.3 Hz, 1H, 5-H in indenyl), 6.88-6.91 (m, 2H, 2,6-H in p-tolyl), 6.53-6.57 (m, 2H, 3,5-H in p-tolyl), 6.52 (m, 1H, 3-H in indenyl), 3.68 (br.s, 1H, NH), 3.40 (s, 2H, 1,1′-H in indenyl), 2.20 (s, 3H, 4-Me in p-tolyl), 2.16 (m, 3H, 2-Me in indenyl), 0.57 (s, 6H, SiMe2). Anal. Calc. for C19H23NSi: C, 77.76; H, 7.90; N, 4.77%. Found: C, 77.94; H, 8.05; N, 4.94%.

후처리

  1. temperaturecooled to −40° C.
  2. stirringThe resulting mixture was stirred for 12 hours at room temperature
  3. customevaporated to dryness
  4. additionTo the residue 100 mL of ether was added
  5. stirringthe obtained suspension was stirred for 20 minutes
  6. filtrationfiltered through glass frit (G3)
  7. washThe precipitate was additionally washed with 2×100 mL of ether
  8. customThe combined filtrate was evaporated to dryness
  9. washthe residue was washed with 2×15 mL of cold hexanes
  10. customdried in vacuum

출처 및 근거

ORD 기록
ord-4f884e62b56e479e9486c2a5c7e3a30d
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058461B2

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