Dimethylformamide → 2-(1-Adamantyl)-4-bromo-1-decyloxybenzene

HRID 256784

反応式

HRID 256784 の反応式
[H-].[Na+].[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.I[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CN(C=O)C>C1COCC1.O>[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 163141-IododecaneHCID 24758Sodium hydrideHCID 46704942-(1-Adamantyl)-4-bromophenol

生成物 1

HCID 136335522-(1-Adamantyl)-4-bromo-1-decyloxybenzene収率 96%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium hydride (80% in oil, 3.2 g, 104 mmol) in 100 ml of THF, there is slowly added a solution of 2-(1-adamantyl)-4-bromophenol (29 g, 95 mmol) in 200 ml of THF. The mixture is stirred until the evolution of gas ceases at which point 27.8 g (23 ml, 104 mmol) of 1-iododecane and 100 ml of DMF are added. The mixture it stirred for 12 hours at ambient temperature, poured into water, extracted with ether, dried and the solvents evaporated. The resulting residue is purified by passage through a silica column (eluant: heptane), yielding 40.7 g (96%) of 2(1-adamantyl)-4-bromo-1-decyloxybenzene. Melting point: 69°-70° C.

後処理

  1. additionare added
  2. extractionextracted with ether
  3. customdried
  4. customthe solvents evaporated
  5. customThe resulting residue is purified by passage through a silica column (eluant: heptane)

出典と根拠

ORDレコード
ord-10c8d6b9c94d433090264c2ea8744d7e
出典データセット
uspto-grants-1993_11
特許番号
USRE034440

関連ノート

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