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

HRID 613359
ノート
印刷プレビュー

反応式

HRID 613359 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 acetatehexane 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 acetatehexane 1:3)

出典と根拠

ORDレコード
ord-88d1c4cc2a814a518e7b8545e9783259
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06008224

反応ノート

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