Ethanol → Bromo-PEG4-t-butyl ester

HRID 2083890노트

반응식

HRID 2083890 반응식
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20]O)([CH3:4])([CH3:3])[CH3:2].C(O)C.C(Br)(Br)(Br)[Br:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][Br:27])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 702EthanolHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11174684Hydroxy-PEG4-t-butyl ester

생성물 1

HCID 12082266Bromo-PEG4-t-butyl ester수율 47.5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

Alternatively, 1.61 g (5.03 mmol) of 9a was co-evaporated successively with 100% ethanol and toluene, then dried over anhydrous sodium sulfate and 4A molecular sieves in dichloromethane. The mixture was filtered and concentrated. To the dried compound (1.42 g) in 20 ml of dichloromethane was added 2.48 g of carbontetrabromide (CBr4, 7.47 mmol) and 1.50 g of triphenylphosphine (PPh3, 5.71 mmol). After stirring under an atmosphere of argon overnight, the reaction mixture was filtered through a silica gel bed, then concentrated and purified by silica gel chromatography. (EtOAc/Hexane Gradient starting at a ratio of 1:2 and changing to a ratio of 2:3) to yield 0.92 g of the 10a. (62%). Rf=0.64 (EtOAc); 1H NMR (CDCl3) 3.785 (t, 2H, J=6.3+6.3 Hz), 3.68 (t, 2H, J=6.5+6.5 Hz), 3.650 (m, 8H), 3.615 (m, 4H), 3.462 (t, 2H, J=6.3+6.4 Hz), 2.491 (t, 2H, J=6.5+6.5 Hz), 1.434 (s, 9H); 13C NMR 171.063, 80.656, 71.368, 70.831, 70.764, 70.706, 70.678, 70.545, 67.061, 36.431, 30.474, 28.263; MS m/z 408.74 (M+Na)+, 406.70, 405.70, 404.73.

후처리

  1. dry with materialdried over anhydrous sodium sulfate and 4A molecular sieves in dichloromethane
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. filtrationthe reaction mixture was filtered through a silica gel bed
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-b9175af2ab01437f8ad6dcf64f469d53
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716821B2

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