Sodium Iodide → HCID 67187886、化合物

HRID 1454357ノート

反応式

HRID 1454357 の反応式
[CH2:1]([O:8][C:9](=[O:26])[CH2:10][CH2:11][C:12](=[CH2:25])[CH2:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.CC([O-])=O.[Na+].[Na+].[I-:39].CC1C=CC(S(NCl)(=O)=O)=CC=1>C1COCC1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][CH:12]([CH2:25][I:39])[CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 5

HCID 5238Sodium IodideHCID 31388TosylchloramideHCID 517045Sodium AcetateHCID 2723981Borane;tetrahydrofuranHCID 67191800Dibenzyl-4-methyleneheptanedioate

生成物 1

HCID 67187886HCID 67187886、化合物収率 35.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Compound B4 (176 mg, 0.5 mmol) was dissolved in anhydrous THF (0.5 mL). The solution was cooled to 0° C. and BH3-THF (2.0 M, 0.25 mL, 0.5 mmol) was added via a syringe. The solution was then stirred at room temperature for 1 h. Methanolic NaOAc (3.0 mL, 1.0 M, 3.0 mmol), aqueous NaI (3.0 mL, 1.0 M, 3.0 mmol) and methanolic chloramine-T (6.0 mL, 0.5 M, 3.0 mmol) were added sequentially to the organoborane solution at room temperature. The reaction mixture were stirred for 10 min at room temperature and then quenched with aqueous Na2S2O3 (1.0 M). The mixture was partitioned between Et2O (50 mL) and H2O (50 mL) and the organic layer was washed with brine (30 mL) before drying over Na2SO4. The solvent was evaporated and the residue was subjected to silica chromatography (CH2Cl2/hexanes, 2/100 to 7/100) to yield compound 1b (85 mg). The yield was 35%. 1H NMR (200 MHz, CDCl3) δ 7.37 (m, 10H), 5.11 (s, 4H), 3.21 (d, 2H, J=8.0 Hz), 2.37 (m, 4H), 1.68 (m, 4H), 1.20 (m, 1H); 13C NMR (50 MHz, CDCl3) δ 173.2, 136.3, 129.1, 128.8, 66.9, 37.5, 31.8, 29.9, 14.5; MS (MALDI-TOF) calcd (M+Na+) 503.3, found 503.8.

後処理

  1. stirringThe reaction mixture were stirred for 10 min at room temperature
  2. customquenched with aqueous Na2S2O3 (1.0 M)
  3. customThe mixture was partitioned between Et2O (50 mL) and H2O (50 mL)
  4. washthe organic layer was washed with brine (30 mL)
  5. dry with materialbefore drying over Na2SO4
  6. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-ce6e4a5642ef4567b7cc37c35d23c2b6
出典データセット
uspto-grants-2009_01
特許番号
US07479548B1

反応ノート

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