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Diethyl Ether → 1-(2-Benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane

HRID 1250274
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HRID 1250274 반응식
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]1([CH3:19])[CH2:18][O:17][CH2:16]1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FB(F)F.C(OCC)C.C(N(CC)CC)C.C(OCC)C>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][C:11]12[O:12][CH2:16][C:15]([CH3:19])([CH2:14][O:13]1)[CH2:18][O:17]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 541789563-Methyl-3-oxetanylmethyl 3-benzyloxypropionate

생성물 1

HCID 183273631-(2-Benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane수율 73.9%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
-15 °C

실험 절차

3-Methyl-3-oxetanylmethyl 3-benzyloxypropionate (521 mg) was dissolved in dichloromethane under an argon atmosphere, and trifluoroborane-diethylether was added thereto at −15° C. The mixture was stirred for 5 hours at −15° C. Triethylamine (280 μl) was added to the reaction mixture, and stirring was continued for 15 minutes. Subsequently, diethylether (3 ml) was added. The precipitating crystals were removed from the reaction mixture by filtration, then the mother liquid was concentrated under reduced pressure. The residue was purified by alumina column chromatography (ethyl acetate-hexane 1:3), to give 385 mg of 1-(2-benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane as a colorless solid.

후처리

  1. customat −15° C
  2. stirringstirring
  3. waitwas continued for 15 minutes
  4. customThe precipitating crystals were removed from the reaction mixture by filtration
  5. concentrationthe mother liquid was concentrated under reduced pressure
  6. customThe residue was purified by alumina column chromatography (ethyl acetate-hexane 1:3)

출처 및 근거

ORD 기록
ord-8e0f52b290c149be9b98bd030643b5fc
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06337334B1

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