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

HRID 18826Notes

Reaction equation

HRID 18826 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-0df910265dde4c77bbc68820210fb1a0
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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