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Acetic Acid → 6-[(Z)-2-(3,4,5-Trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene

HRID 218242
ノート
印刷プレビュー

反応式

HRID 218242 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]\[C:15]2[C:20]([O:21][Si](C(C)(C)C)(C)C)=[C:19]([O:29][Si](C(C)(C)C)(C)C)[CH:18]=[CH:17][CH:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[CH:13]=[CH:14]\[C:15]2[C:20]([OH:21])=[C:19]([OH:29])[CH:18]=[CH:17][CH:16]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]
参加物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 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 601306896-[(Z)-2-(3,4,5-Trimethoxyphenyl)vinyl]-1,2-di(tert-butyldimethylsilyloxy) benzene

生成物 1

HCID 99721426-[(Z)-2-(3,4,5-Trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene収率 94.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

A solution of 8 (0.106 g, 0.2 mmol) in 2 mL THF was stirred at 0° while adding acetic acid (0.024 g, 0.4 mmol) and tetrabutylammonium fluoride (1M in THF, 0.4 ml, 0.4 mmol). The solution was stirred at 20° for one hour then cooled to 0° and 0.5 mL water added. The mixture was extracted with TBME three times, dried, evaporated and the residue partitioned between 10 mL heptane/10 mL acetonitrile. Evaporation of the acetonitrile layer gave 0.057 g pale yellow gum which was purified by silica chromatography with 7:3 heptane:ethyl acetate to give ZSB-82 as a colourless gum (0.032 g):

後処理

  1. temperaturethen cooled to 0°
  2. extractionThe mixture was extracted with TBME three times
  3. customdried
  4. customevaporated
  5. customthe residue partitioned between 10 mL heptane/10 mL acetonitrile
  6. customEvaporation of the acetonitrile layer

出典と根拠

ORDレコード
ord-6a871dd083a145b58d35addf9de6b527
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08198302B2

反応ノート

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