Sodium hydride → HCID 19966068、化合物

HRID 977853ノート

反応式

HRID 977853 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 19966068HCID 19966068、化合物収率 89%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7a57a676e1bc43c9b5b2a8809fed5ce9
出典データセット
uspto-grants-1997_03
特許番号
US05614550

反応ノート

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