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2-Benzyloxybenzoic acid → (1R)-1-Methyl-2-(tert-butyldimethylsiloxy)ethyl 2-(phenylmethoxy)benzoate

HRID 1392588
ノート
印刷プレビュー

反応式

HRID 1392588 の反応式
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:18]([CH2:26][C@H:27](O)[CH3:28])[Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([O:13][C@H:27]([CH3:28])[CH2:26][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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 18105812-Benzyloxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol

生成物 1

HCID 60207254(1R)-1-Methyl-2-(tert-butyldimethylsiloxy)ethyl 2-(phenylmethoxy)benzoate収率 29.1%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(phenylmethoxy)benzoic acid (4.0 g, 17.5 mmol), (2R)-1-(tert-butyldimethylsiloxy)propan-2-ol (2.78 g, 14.6 mmol), and 4-(dimethylamino)pyridine (183 mg) in 100 mL of anhydrous dichloromethane, 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (EDAC) (4.2 g, 17.5 mmol) was slowly added. The resulting mixture was stirred at room temperature for 48 hrs. The reaction mixture was diluted with dichloromethane and washed with 0.5N HCl twice followed by the addition of saturated NaHCO3 solution and brine. The organic layer was separated, dried through a MgSO4 pad, and concentrated under reduced pressure. Chromatography (silica gel, 1:12 ethyl acetate/hexane) of the residue afforded 1.7 g (29%) of (1R)-1-Methyl-2-(tert-butyldimethylsiloxy)ethyl 2-(phenylmethoxy)benzoate.

後処理

  1. washwashed with 0.5N HCl
  2. additiontwice followed by the addition of saturated NaHCO3 solution and brine
  3. customThe organic layer was separated
  4. dry with materialdried through a MgSO4 pad
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-408e69f1dab34fbbb81d55be51eec552
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07342131B2

反応ノート

読み込み中…

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