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Imidazole → [5-Bromo-1-(1-propylcyclobutyl)pent-3-enyloxy]tert-butyldimethylsilane

HRID 2249574
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HRID 2249574 반응식
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Si:27]([O:34][CH:35]([C:41]1([CH2:45][CH2:46][CH3:47])[CH2:44][CH2:43][CH2:42]1)[CH2:36][CH:37]=[CH:38][CH2:39]O)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>C(Cl)Cl.CCCCCC>[Br:1][CH2:39][CH:38]=[CH:37][CH2:36][CH:35]([C:41]1([CH2:45][CH2:46][CH3:47])[CH2:44][CH2:43][CH2:42]1)[O:34][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 671021205-(Tert-butyldimethylsilanyloxy)-5-(1-propylcyclobutyl)pent-2-en-1-ol

생성물 1

HCID 67101903[5-Bromo-1-(1-propylcyclobutyl)pent-3-enyloxy]tert-butyldimethylsilane수율 86.5%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
2회
HCID 8058Hexane용매

실험 절차

Bromine (0.17 mL, 3.22 mmol) was added to a solution of triphenylphosphine (844 mg, 3.22 mmol) and imidazole (219 mg, 3.22 mmol) in CH2Cl2 (11.0 mL) at 23° C. After 0.5 h a solution of the alcohol 7 (838 mg, 2.68 mmol) in CH2Cl2 (2.7 mL) was added. The reaction was stirred for 1 h, diluted with hexane and then filtered through celite. The filtrate was concentrated in vacuo and purified by FCC (silica gel, 100% hex) to give 870 mg (86%) of the bromide 8 as a clear, light yellow oil.

후처리

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by FCC (silica gel, 100% hex)

출처 및 근거

ORD 기록
ord-c85713b7e4ee41cea91b1e15a54ab977
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07314890B2

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