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

HRID 1468231노트

반응식

HRID 1468231 반응식
[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

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 3382465Tert-ButanesulfinamideHCID 581971077'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-one2회

생성물 1

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

시약·촉매·용매 2

HCID 76524Titanium tetraethoxide촉매HCID 962Water용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-d83022f744a14a8a8b121e79dd443ffa
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000184B2

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