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

HRID 18826

반응식

HRID 18826 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-0df910265dde4c77bbc68820210fb1a0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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