1,2-Dibromoethane → HCID 54310569、化合物

HRID 654949ノート

反応式

HRID 654949 の反応式
[O:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Mg]Br)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].BrCCCCCCCCO[Si](C(C)(C)C)(C)C.[Mg].BrCCBr.[CH3:41][Si:42]([CH3:51])([CH3:50])[C:43]1[O:47][CH:46]=[C:45]([CH:48]=[O:49])[CH:44]=1>O1CCCC1>[OH:49][CH:48]([C:45]1[CH:44]=[C:43]([Si:42]([CH3:51])([CH3:50])[CH3:41])[O:47][CH:46]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:1][Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

参加物

7

反応物 5

HCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 10969362Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178455211HCID 178455211、化合物

生成物 1

HCID 54310569HCID 54310569、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 8-t-butyldimethylsiloxyoctylmagnesium bromide (5.63 mmol prepared from 1-bromo-8-t-butyldimethylsiloxyoctane 1.82 g, 5.63 mmol and 6.19 mmol magnesium; with a catalytic amount of 1,2-dibromoethane as initiator) in tetrahydrofuran (2 ml) at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.866 g, 5.15 mmol) in tetrahydrofuran (10 ml). The solution was warmed to room temperature, stirred for one hour, quenched with cold 10% hydrochloric acid and extracted into ethyl ether. The organic portion was washed with saturated sodium bicarbonate, water saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a pale oil. Purification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane) gave the desired alcohol.

後処理

  1. customquenched with cold 10% hydrochloric acid
  2. extractionextracted into ethyl ether
  3. washThe organic portion was washed with saturated sodium bicarbonate, water saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a pale oil
  8. customPurification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-7886fa1c1d4a47ed87b017fd930a3747
出典データセット
uspto-grants-1992_07
特許番号
US05134128

反応ノート

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