Water → N-(5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamide

HRID 539348

反応式

HRID 539348 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2([OH:18])[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]2)=O)[CH:7]=1.[CH3:20][C:21]([S:24]([NH2:26])=[O:25])([CH3:23])[CH3:22].O>CN1C2C(N=C(N)NC=2NCC1CNC1C=CC(C(NC(C(O)=O)CCC(O)=O)=O)=CC=1)=O.CCOC(C)=O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][C:10]3([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]3)[C:8](=[N:26][S:24]([C:21]([CH3:23])([CH3:22])[CH3:20])=[O:25])[C:6]=2[CH:7]=1

参加物

7

反応物 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 67979505(5-Bromo-2-fluorophenyl)(1-hydroxy-4-methoxycyclohexyl)methanone2 回

生成物 1

HCID 67979520N-(5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamide収率 65%

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 8857Ethyl Acetate溶媒HCID 178479889HCID 178479889、化合物溶媒

実験手順

To a mixture of 5-bromo-4′-methoxy-3H-spiro[benzofuran-2,1′-cyclohexan]-3-one (Intermediate 12, 2.8 g, 9.00 mmol) and 2-methylpropane-2-sulfinamide (2.024 g, 16.20 mmol) in methyl THF (15 mL) was added titanium ethoxide (3.71 mL, 18.00 mmol) and the reaction was heated to reflux. After 21 h the reaction was allowed to cool to r.t. whereafter it was diluted with EtOAc (150 mL). Water (12 mL) was added dropwise over 10 min under vigorous stirring and then the mixture was left standing without stirring for 1.5 h. The solids were filtered off and the organics were evaporated. The crude product was purified by flash chromatography using a gradient of 0%-50% EtOAc in heptane, yielding 2.41 g of the title compound (65% yield): 1H NMR (500 MHz, CDCl3) δ ppm 1.33 (s, 9 H), 1.81 (m, 6 H), 2.12 (d, 2 H), 3.33 (m, 1 H), 3.42 (s, 3 H), 6.94 (d, 1 H), 7.59 (dd, 1 H), 8.53 (m, 1 H); MS (ES+) m/z 415 [M+H]+.

後処理

  1. temperaturethe reaction was heated to reflux
  2. waitthe mixture was left
  3. stirringwithout stirring for 1.5 h
  4. filtrationThe solids were filtered off
  5. customthe organics were evaporated
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-8c27dd4fceca4ead89fb8c6b2efb2e63
出典データセット
uspto-grants-2014_10
特許番号
US08865911B2

関連ノート

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