Triphenyl(3,4,5-trimethoxybenzyl)phosphonium bromide → 4-Bromo-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-di(tert-butyldimethylsilyloxy)benzene

HRID 218251노트

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HRID 218251 반응식
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[Si:39]([O:46][C:47]1[C:54]([O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])=[CH:53][C:52]([Br:63])=[CH:51][C:48]=1[CH:49]=O)([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40]>O1CCCC1.CCCCCC.C(OC)(C)(C)C>[Br:63][C:52]1[CH:51]=[C:48](/[CH:49]=[CH:7]\[C:6]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:4]([O:3][CH3:2])[CH:5]=2)[C:47]([O:46][Si:39]([C:42]([CH3:45])([CH3:43])[CH3:44])([CH3:41])[CH3:40])=[C:54]([O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:57])[CH3:58])[CH:53]=1

참가 물질

7

반응물 3

HCID 370917Triphenyl(3,4,5-trimethoxybenzyl)phosphonium bromideHCID 60130680HCID 60130680, 화합물HCID 178418339Butyllithium

생성물 1

HCID 601306724-Bromo-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-di(tert-butyldimethylsilyloxy)benzene수율 55.9%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 15413tert-Butyl methyl ether용매

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온도
0 °C

실험 절차

A suspension of 3,4,5-trimethoxybenzyltriphenylphosphonium bromide (1.69 g, 3.23 mmol) in tetrahydrofuran (30 mL) was cooled to 0° C. and butyllithium (2 mL of a 1.6 N solution in hexane, 3.23 mmol) was added dropwise. The brick red solution was stirred at 0° C. for 20 min, then a solution of 19 (0.96 g, ca 2.2 mmol) in tetrahydrofuran (12 mL) was added dropwise. The temperature was allowed to rise to room temperature overnight, than the reaction was diluted with tert-butylmethyl ether (ca 100 mL) and washed with water (ca 50 mL, containing 1 mL 2N HCl) then brine (30 mL). The organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give a crude which was purified by column (elution with cyclohexane:AcOEt 10:1) to give 0.75 g of 20 still impure with 20% of the E isomer.

후처리

  1. waitto rise to room temperature overnight, than the reaction
  2. washwashed with water (ca 50 mL, containing 1 mL 2N HCl)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customthe solvent removed under reduced pressure
  5. customto give a crude which
  6. customwas purified by column (elution with cyclohexane:AcOEt 10:1)

출처 및 근거

ORD 기록
ord-ae5a82024ead43189050401038470273
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198302B2

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