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Triethylamine → Methyl 4-[2-(benzotriazol-1-yloxycarbonyl)-vinyl]-benzoate

HRID 1180801
ノート
印刷プレビュー

反応式

HRID 1180801 の反応式
[C:1]([CH:4]=[CH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)([OH:3])=[O:2].CCN(CC)CC.CN([P+](O[N:34]1[N:42]=[N:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[N:41]1([O:2][C:1]([CH:4]=[CH:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=2)=[O:3])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[N:42]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 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 86881Benzoic acid, 4-(2-carboxyethenyl)-, methyl esterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

生成物 1

HCID 72479810Methyl 4-[2-(benzotriazol-1-yloxycarbonyl)-vinyl]-benzoate収率 84%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution at room temperature of VII (264 mg, 1.28 mmol) in anhydrous DMF (10 ml) under nitrogen were added Et3N (196 μl, 1.41 mmol) and BOP reagent (680 mg, 1.1.54 mmol), respectively. After few min, a precipitate appeared. After 3 h, the reaction mixture was poured into a saturated aqueous solution of NH4Cl, and diluted with AcOEt. After separation, the organic layer was successively washed with sat NH4Cl, H2O and brine, concentrated a little bit, and hexane was added. The suspension was filtered off and rinsed with hexane. The solid was triturated in water, filtered off, rinsed with water, and dried to afford the title compound VIII (346 mg, 1.07 mmol, 84% yield) as a pale yellow solid (not stable on silica gel !). 1H NMR (300 MHz, CDCl3) δ(ppm): 8.56 (d, J=8.3 Hz, 1H), 8.21–8.02 (m, 3H), 7.90–7.72 (m, 4H), 7.62 (t, J=7.4 Hz, 1H), 3.97 (s, 3H).

後処理

  1. customAfter separation
  2. washthe organic layer was successively washed with sat NH4Cl, H2O and brine
  3. concentrationconcentrated a little bit, and hexane
  4. additionwas added
  5. filtrationThe suspension was filtered off
  6. washrinsed with hexane
  7. customThe solid was triturated in water
  8. filtrationfiltered off
  9. washrinsed with water
  10. customdried

出典と根拠

ORDレコード
ord-b1cd1211c3ba4805bf348d7d224f7f9b
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07282608B2

反応ノート

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