Ethyl Acetate → N-(7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalene]-1'-ylidene)-2-methylpropane-2-sulfinamide

HRID 1468231ノート

反応式

HRID 1468231 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:17][CH2:16][CH:15]([O:18][CH3:19])[CH2:14][CH2:13]3)[C:9]2=O)=[CH:4][CH:3]=1.[CH3:20][C:21]([S:24]([NH2:26])=[O:25])([CH3:23])[CH3:22].CCOC(C)=O>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:17][CH2:16][CH:15]([O:18][CH3:19])[CH2:14][CH2:13]3)[C:9]2=[N:26][S:24]([C:21]([CH3:23])([CH3:22])[CH3:20])=[O:25])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 3382465Tert-ButanesulfinamideHCID 581971077'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-one2 回

生成物 1

HCID 86706708N-(7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalene]-1'-ylidene)-2-methylpropane-2-sulfinamide収率 20.5%

試薬・触媒・溶媒 2

HCID 76524Titanium tetraethoxide触媒HCID 962Water溶媒

実験手順

7′-Bromo-4-methoxy-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-naphthalen]-1′-one (Intermediate 9, 2.26 g, 6.99 mmol), 2-methylpropane-2-sulfinamide (1.27 g, 10.5 mmol) and titanium ethoxide (2.88 mL, 14.0 mmol) were dissolved in 2-Me THF (15 mL) and heated to reflux over the weekend. The reaction was stopped and cooled to r.t. EtOAc (30 mL) and water (15 mL) were added under stirring. The mixture was then let to stand without stirring for 1 h. The organic phase was collected by filtration, dried using a phase separator and concentrated in vacuo. The product was purified by flash column chromatography using a gradient of 0-100% EtOAc in heptane to give the title compound (0.61 g, 20% yield): MS (ES+) m/z 426.11 [M+H]+.

後処理

  1. temperatureheated
  2. temperatureto reflux over the weekend
  3. stirringwithout stirring for 1 h
  4. filtrationThe organic phase was collected by filtration
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash column chromatography

出典と根拠

ORDレコード
ord-d83022f744a14a8a8b121e79dd443ffa
出典データセット
uspto-grants-2015_04
特許番号
US09000184B2

反応ノート

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