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

HRID 2053617Notes

Reaction equation

HRID 2053617 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, 4H), 4.0 (m, 1H), 3.6-3.4 (m, 4H), 1.85 (m, 1H), 1.6-1.3 (m, 5H), 1.25 (t, 3H); 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-68553e56b2ec4b41a8a050f5f3bd9261
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

Loading…