Sodium Hydroxide → (-)-5-Decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine

HRID 1956084ノート

反応式

HRID 1956084 の反応式
[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].[OH:27][CH:28]([CH3:34])[CH2:29][CH2:30][CH2:31][C:32]#[CH:33].[B]1OC2C(=CC=CC=2)O1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH:33]=[CH:32][CH2:31][CH2:30][CH2:29][CH:28]([OH:27])[CH3:34])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

参加物

9

反応物 4

HCID 14798Sodium HydroxideHCID 6327445BenzcatechinboraneHCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 133371736-Heptyn-2-ol

生成物 1

HCID 53726462(-)-5-Decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a reactor equipped with a stirrer and a thermometer, 5-decyloxy-2-(4-bromophenyl)pyrimidine (13.98 g), dry tetrahydrofuran (THF) (30 ml), tetrakis(triphenylphosphine)palladium (0.11 g) and sodium hydroxide (1.2 g) are charged. To the mixture, a solution of a reaction product of 6-hydroxy-1-heptyne and catechol borane (5 g) dissolved in THF (12 ml) is dropwise added, followed by heating up to a refluxing temperatur. After reacting for 4 hours, the reaction mixture is cooled to room temperature. To the mixture, toluene and water are added for extraction, and the organic layer is washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine (7.99 g).

後処理

  1. customIn a reactor equipped with a stirrer
  2. additionis dropwise added
  3. temperatureby heating up to a refluxing temperatur
  4. washthe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customA resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

出典と根拠

ORDレコード
ord-8a8ce80cea944b04bf606a5037419e41
出典データセット
uspto-grants-1998_07
特許番号
US05779934

反応ノート

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