Triphenylphosphine → 2-(2-Bromoethyl)cyclopropylmethyl t-butyldimethyl silyl ether

HRID 36809

반응식

HRID 36809 반응식
[Si:1]([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[CH2:13][CH2:14]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:35]Br.C(=O)([O-])O.[Na+]>CN(C)C=O>[Si:1]([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[CH2:13][CH2:14][Br:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 199378982-(2-Hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether

생성물 1

HCID 217604272-(2-Bromoethyl)cyclopropylmethyl t-butyldimethyl silyl ether수율 14.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
-20 °C

실험 절차

2-(2-hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether (15.0 g, 65 mmol) was dissolved in N,N-dimethylformamide (120 ml), and triphenylphosphine (17.3 g, 66 mmol) was added thereto at room temperature. Twenty minutes later, the mixture was cooled to -20° C. Bromine (10.5 g, 66 mmol) was added thereto over a period of 5 minutes, and the temperature was gradually raised to 0° C. The mixture was poured into a saturated sodium hydrogen carbonate aqueous solution, and the product was extracted with ethyl ether. Then, it was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain 2-(2-bromoethyl)cyclopropylmethyl t-butyldimethylsilyl ether (2.7 g).

후처리

  1. customat room temperature
  2. temperaturethe temperature was gradually raised to 0° C
  3. extractionthe product was extracted with ethyl ether
  4. dry with materialThen, it was dried over anhydrous magnesium sulfate
  5. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d890c419f22941b6b3aede17a4928400
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416231

연결된 노트

불러오는 중…