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Ethyl Acetate → HCID 178481818、化合物

HRID 271305
ノート
印刷プレビュー

反応式

HRID 271305 の反応式
[C:1]([S:5]([NH2:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Cl:8][C:9]1[CH2:10][CH:11]2[C:32](=O)[CH:14]([CH2:15][C:16]=1/[CH:17]=[CH:18]/[C:19]1[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:21]([CH3:31])[N:20]=1)[CH2:13][CH2:12]2.C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:8][C:9]1[CH2:10][CH:11]2[CH2:12][CH2:13][CH:14](/[C:32]/2=[N:7]/[S:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[O:6])[CH2:15][C:16]=1/[CH:17]=[CH:18]/[C:19]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:21]([CH3:31])[N:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 3382465Tert-ButanesulfinamideHCID 693100833-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one

生成物 1

HCID 178481818HCID 178481818、化合物収率 99.5%

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒
HCID 8028
Tetrahydrofuran
溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

tert-Butylsulphinamide (3.0, 24 mmol) followed by titanium (IV) ethoxide (4.6 ml, 36 mmol) was added to a stirring solution of the product of Step 3 (4.56 g, 11 mmol) in dry THF (10 ml) and the resulting solution was heated to reflux for 18 hrs. The reaction was poured into a stirring solution of brine (200 ml) and then ethyl acetate (100 ml) was added and the mixture filtered through celite. The filtrate was partitioned and the aqueous layer was further extracted with ethyl acetate (2×50 ml). The combined organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo, to afford N((9Z)-3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-ylidene)-2-methylpropane-2-sulfinamide (5.19 g, 99%). m/z (ES+) 474 (MH)+. Compound taken directly onto next Step.

後処理

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 18 hrs
  3. filtrationthe mixture filtered through celite
  4. customThe filtrate was partitioned
  5. extractionthe aqueous layer was further extracted with ethyl acetate (2×50 ml)
  6. extractionThe combined organic extract
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0c6df90edbba416b8afb216f35002d16
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07452899B2

反応ノート

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