Methanol → (Tetrahydropyran-2-yl)methoxyacetic Acid Ethyl Ester

HRID 18826

反応式

HRID 18826 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-].CO>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][O:8][CH2:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH3:16]

参加物

6

反応物 3

HCID 887MethanolHCID 7524Tetrahydropyran-2-methanolHCID 12192Ethyl diazoacetate

生成物 1

HCID 43119671(Tetrahydropyran-2-yl)methoxyacetic Acid Ethyl Ester収率 82.1%

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of tetrahydropyran-2-methanol (1.13 mL, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (11 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at rt for 20 min. To the reaction mixture is added MeOH (0.5 mL), and the solvents rotary evaporated. The residue is purified by chromatography on silica gel; elution with EtOAc:heptane (30:70) gives 1.66 g of the product 458. 1H NMR (CDCl3) δ 4.3-4.1 (m, 4 H), 4.0 (m, 1 H), 3.6-3.4 (m, 4 H), 1.85 (m, 1 H), 1.6-1.3 (m, 5 H), 1.25 (t, 3 H); MS: m/z 203 (M++1).

後処理

  1. customThe residue is purified by chromatography on silica gel
  2. washelution with EtOAc:heptane (30:70)

出典と根拠

ORDレコード
ord-0df910265dde4c77bbc68820210fb1a0
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

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