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

HRID 1250274
ノート
印刷プレビュー

反応式

HRID 1250274 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
-15 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8e0f52b290c149be9b98bd030643b5fc
出典データセット
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06337334B1

反応ノート

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