Ethyl diazoacetate → HCID 68570639, compound

HRID 2053616Notes

Reaction equation

HRID 2053616 reaction equation
[O:1]1[CH2:6][CH:5](O)[CH2:4][O:3][CH2:2]1.[N+](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH:5]1[CH2:6][O:1][CH2:2][O:3][CH2:4]1)[CH3:15]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 784751,3-Dioxan-5-ol

Product 1

HCID 68570639HCID 68570639, compoundYield 41.3%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 1,3-dioxan-5-ol (1.04 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.03 mmol). The reaction mixture is stirred at rt for 4 h. The reaction mixture is diluted with heptane and filtered. The filtrate is evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (1:4) gives 0.65 g of the product 454. 1H NMR (CDCl3) δ 5.04 (s, 1H), 4.89 (s, 1H), 4.25-4.20 (m, 5H), 3.98 (dd, 1H), 3.78 (dd, 1H), 3.65 (d, 1H), 1.29 (t, 3H)

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe residue is purified by chromatography on silica gel
  4. washelution with EtOAc:heptane (1:4)

Sources & evidence

ORD record
ord-28d6c4c2a51848fba4a8c4f830053763
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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