Hydrochloric Acid → HCID 9903422、化合物

HRID 377195ノート

反応式

HRID 377195 の反応式
C([O:8][C:9]([CH:11]([CH2:25][CH2:26][C:27]([O:29]CC1C=CC=CC=1)=[O:28])[CH2:12][P:13]([CH2:16][CH2:17][CH2:18][C:19]1C=CC=CC=1)(=[O:15])[OH:14])=[O:10])C1C=CC=CC=1.[H-].[Na+].C=C(CCC(OCC1C=CC=CC=1)=O)C(OCC1C=CC=CC=1)=O.Cl>C1COCC1.CCOC(C)=O>[CH2:16]([P:13]([CH2:12][CH:11]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[C:9]([OH:10])=[O:8])([OH:15])=[O:14])[CH2:17][CH2:18][CH3:19]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10947302Dibenzyl 2-methylenepentanedioateHCID 18403163HCID 18403163、化合物

生成物 1

HCID 9903422HCID 9903422、化合物収率 154.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-methylbenzyl-O-benzylphosphinic acid (2, R=4-methylbenzyl)(2.16 g, 8.3 mmol) in THF (15 mL) was added sodium hydride (0.10 g, 60% dispersion in oil) followed by dibenzyl 2-methylenepentanedioate at 0 C, and the mixture was stirred at rt for 4 h. The reaction mixture was then diluted with EtOAc (50 mL) and poured into 1N HCl (50 mL). The organic layer was separated, dried over Na2SO4, and concentrated. This material was purified by silica gel chromatography (hexanes: EtOAc, 4:1 to 1:1) to give 3.41 g of 2,4-di(benzyloxycarbonyl)butyl(4-methylbenzyl)-o-benzylphosphinic acid (4, R=4-methylbenzyl) as colorless oil (70% yield): Rf 0.61 (EtOAc); 1H NMR (CDCl3) delta 1.6-1.8 (m, 1 H), 1.9-2.0 (m, 2 H), 2.1-2.4 (m, 6 H), 2.7-2.9 (m, 1 H), 3.05 (dd, J=9.0, 16.8 Hz, 2 H), 4.8-5.1 (m, 6 H), 7.0-7.1 (m, 4 H), 7.2-7.4 (m, 15 H).

後処理

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThis material was purified by silica gel chromatography (hexanes: EtOAc, 4:1 to 1:1)

出典と根拠

ORDレコード
ord-d027454c494d4b0c8e42f7ca0932b00b
出典データセット
uspto-grants-2000_02
特許番号
US06025345

反応ノート

読み込み中…