3,4-dihydro-2H-pyran → HCID 178418655、化合物

HRID 5303

反応式

HRID 5303 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.S(O[Si](C)(C)C)(O[Si](C)(C)C)(=O)=O>ClCCl>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 87573Silanol, trimethyl-, 1,1'-sulfateHCID 178418615HCID 178418615、化合物

生成物 1

HCID 178418655HCID 178418655、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether.

後処理

  1. washwashed once with sodium carbonate solution and twice with water
  2. dry with materialsubsequently dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
  6. customRecrystallization from ethyl acetate at -20° C.

出典と根拠

ORDレコード
ord-5e5c25f893b444bd9bf8ae43f97a4d3f
出典データセット
uspto-grants-1993_09
特許番号
US05244597

関連ノート

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