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Ethyl Acetate → Benzyl 3-(2-propionyloxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoate

HRID 39278
ノート
印刷プレビュー

反応式

HRID 39278 の反応式
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([P:13]([O:24][CH2:25][CH3:26])([CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])=[O:14])=[CH:9][C:8]=1[C:27]([CH3:40])([CH3:39])[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(OCC)(=O)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([P:13]([O:24][CH2:25][CH3:26])([CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])=[O:14])=[CH:9][C:8]=1[C:27]([CH3:40])([CH3:39])[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])(=[O:4])[CH2:2][CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 62324Propionyl chlorideHCID 25139361Benzyl 3-(2-hydroxy-5-(Ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoate

生成物 1

HCID 86655577Benzyl 3-(2-propionyloxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoate収率 66.2%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 1049Pyridine溶媒

実験手順

Proprionyl chloride (190 μL, 2.17 mmol) was added drop-wise to a stirring solution of crude phenol 122 (880 mg, 1.67 mmol) and DMAP (2 mg, 0.016 mmol) in pyridine (5 mL). The reaction was continued for 3 hr at room temperature followed by the addition of ethyl acetate (100 mL). The organic layer was washed with cold aqueous HCl (0.5 N), H2O and saturated aqueous NaCl then dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel chromatography (0 to 20% methanol in ethyl acetate) using a Biotage Horizons™ system, resulting in 123 as a pale yellow liquid (644 mg, 66%): 1H NMR (400 MHz, CDCl3) δ 1.25 (t, J=7.0, 3H), 1.26 (t, J=7.5, 3H), 1.30 (t, J=7.0, 3H), 1.46 (s, 3H), 1.48 (s, 3H), 2.50-2.63 (m, 4H), 2.82 (AB q, J=14.4, 2H), 3.93-4.16 (m, 6H), 4.93 (s, 2H), 7.12-7.18 (m, 3H), 7.26-7.32 (m, 3H), 7.70 (ddd, J=1.8, 8.4, 11.6, 1H), 7.86 (dd, J=1.8, 13.4, 1H): 31P (162 MHz, CDCl3) δ 20.21 (d, J=9.7, 1 P), 34.03 (d, J=9.7, 1 P).

後処理

  1. washThe organic layer was washed with cold aqueous HCl (0.5 N), H2O and saturated aqueous NaCl
  2. dry with materialthen dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by silica gel chromatography (0 to 20% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-59f6858b49044c839b8d0114e1657121
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524691B2

反応ノート

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