Sodium hydride → HCID 19966068, 화합물

HRID 1734892노트

반응식

HRID 1734892 반응식
[H-].[Na+].[C:3]1([CH3:15])[CH:8]=[CH:7][C:6]([S:9]([CH2:12][S:13][CH3:14])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:16]1([CH2:22]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl-].[NH4+]>CCCCCC.CN(C)C=O>[CH3:15][C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH:12]([S:13][CH3:14])[CH2:22][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:11])=[O:10])=[CH:7][CH:8]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 137636Cyclohexane, (bromomethyl)-HCID 548421Methylthiomethyl p-tolyl sulfone

생성물 1

HCID 19966068HCID 19966068, 화합물수율 89%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

실험 절차

990 mg (22.7 mmol) of sodium hydride (as a 55% w/w suspension in mineral oil) were washed twice with hexane, and suspended in 40 ml of dimethylformamide. 4.35 g (20.1 mmol) of methylthiomethyl p-tolyl sulfone were added to this suspension and, after 5 minutes, 3.1 ml (22.2 mmol) of cyclohexylmethyl bromide were added. The mixture was allowed to return to room temperature, after which it was stirred for 5 hours. At the end of this time, a dilute aqueous solution of ammonium chloride was added to stop the reaction. The reaction mixture was then extracted with diethyl ether, and the extract was washed with a saturated aqueous solution of sodium chloride. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 100 g of silica gel. Elution with a 1:3 by volume mixture of ethyl acetate and hexane afforded 5.57 g (yield 89%) of the title compound as crystals, melting at 65°-66° C. (after recrystallization from a mixture of diisopropyl ether and hexane)

후처리

  1. customto return to room temperature
  2. customthe reaction
  3. extractionThe reaction mixture was then extracted with diethyl ether
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride
  5. customThe solvent was then removed by distillation under reduced pressure
  6. washElution with a 1:3
  7. additionby volume mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-31e45ace5e8c4234ae2b9ff2f2764ba8
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534529

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