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

HRID 256784

반응식

HRID 256784 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 136335522-(1-Adamantyl)-4-bromo-1-decyloxybenzene수율 96%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-10c8d6b9c94d433090264c2ea8744d7e
출처 데이터셋
uspto-grants-1993_11
특허 번호
USRE034440

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