Potassium Fluoride → P-[Tetrahydropyran-2-yloxy]phenylacetylene

HRID 1020513ノート

反応式

HRID 1020513 の反応式
[F-].[K+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][CH:11]=1>CO>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]#[CH:17])=[CH:14][CH:15]=1

参加物

4

反応物 2

HCID 522689Potassium FluorideHCID 10540306Silane, trimethyl[[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]ethynyl]-

生成物 1

HCID 11310191P-[Tetrahydropyran-2-yloxy]phenylacetylene

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

KF (9.3 g, 160 mmol) was added to a stirred solution of 2 (22.6 g, 80 mmol) in MeOH (150 ml). The reaction mixture was stirred at room temperature for about 4 hours. After the reaction finished (GC shows no starting material remaining), the solvent was removed under reduced pressure on a rotary evaporator. The residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9:1) to give a pale yellow crystals of 3. Yield 15.7 g (97%); mp 65° C., δH(CDCl3, 300 MHz): 7.42 (d, J=8.7, 2H, Ar—H), 7.00 (d, J=8.7, 2H, Ar—H), 5.43 (t, J=3.2, 1H, OCHO), 3.87 (m, 1H, THP), 3.60 (m, 1H, THP), 2.99 (s, 1H, C═C—H), 1.96˜1.56 (m, 6H, THP).

後処理

  1. customwas removed under reduced pressure on a rotary evaporator
  2. customThe residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9:1)
  3. customto give a pale yellow crystals of 3

出典と根拠

ORDレコード
ord-bf965abc6234415b8ab052f66394d1db
出典データセット
uspto-grants-2014_05
特許番号
US08716355B2

反応ノート

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