Lithium Hexamethyldisilazide → t-Butyl-[2-(4,8-dimethyl-non-1-enyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-dimethylsilane

HRID 1810598노트

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HRID 1810598 반응식
Br[CH:2]([PH3+])[CH2:3][CH:4]([CH3:11])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:23]([Si:27]([CH3:46])([CH3:45])[O:28][C:29]1[C:30]([CH3:44])=[C:31]2[C:36](=[C:37]([CH3:40])[C:38]=1[CH3:39])[O:35][C:34]([CH3:43])([CH:41]=O)[CH2:33][CH2:32]2)([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([Si:27]([O:28][C:29]1[C:30]([CH3:44])=[C:31]2[C:36](=[C:37]([CH3:40])[C:38]=1[CH3:39])[O:35][C:34]([CH:41]=[CH:2][CH2:3][CH:4]([CH3:11])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])([CH3:43])[CH2:33][CH2:32]2)([CH3:46])[CH3:45])([CH3:24])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 749761846-(t-Butyl-dimethyl-silyloxy)-2,5,7,8-tetramethyl-chroman-2-carbaldehydeHCID 866467961-Bromo-3,7-dimethyl octanyl phosphonium

생성물 1

HCID 66752470t-Butyl-[2-(4,8-dimethyl-non-1-enyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-dimethylsilane수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

To a suspension of 1-bromo-3,7-dimethyl octanyl phosphonium (1.05 mmol) in 20 mL of anhydrous THF at 0° C. was added 1.05 mL of 1 M lithium bis(trimethysilyl)amide in THF. The mixture was stirred at 0° C. for 30 min, and compound iii (1 mmol) in 10 mL of THF was slowly added over a period of 1 h. After being stirred at room temperature for 1 h, the solution was concentrated, diluted with 20 mL of ethyl acetate, and washed, in tandem, with H2O and brine. The residue was purified by flash silica gel chromatography to afford t-butyl-[2-(4,8-dimethyl-non-1-enyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-dimethylsilane (iv) as colorless oil in 80% yield. 1H NMR (300 MHz, CDCl3) δ 0.11 (s, 6H), 0.86-0.95 (m, 6H), 1.04 (s, 9H), 1.39 (s, 1H), 1.49-1.56 (m, 1H), 1.76-1.86 (m, 1H), 2.01-2.06 (m, 2H), 2.11 (s, 3H), 2.17 (s, 6H), 2.25-2.32 (m, 1H), 2.62 (t, J=6.60 Hz, 2H), 5.30-5.44 (m, 2H).

후처리

  1. stirringAfter being stirred at room temperature for 1 h
  2. concentrationthe solution was concentrated
  3. additiondiluted with 20 mL of ethyl acetate
  4. washwashed, in tandem, with H2O and brine
  5. customThe residue was purified by flash silica gel chromatography

출처 및 근거

ORD 기록
ord-d9009274bb274d37825afc5d16d0bffc
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362071B2

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