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Ethyl diazoacetate → Ethyl (dicyclopropylmethoxy)acetate

HRID 18823
Notes
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Reaction equation

HRID 18823 reaction equation
[CH:1]1([CH:4]([CH:6]2[CH2:8][CH2:7]2)[OH:5])[CH2:3][CH2:2]1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>ClCCl.CCCCCCC.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:5][CH:4]([CH:6]1[CH2:8][CH2:7]1)[CH:1]1[CH2:3][CH2:2]1)[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 84336Dicyclopropylmethanol

Product 1

HCID 22159734Ethyl (dicyclopropylmethoxy)acetateYield 52.1%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent
HCID 8900
Heptane
Solvent

Procedure

To a solution of dicyclopropylmethan-1-ol (1.5 mL, 12.7 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.26 mL, 12.0 mmol). The reaction mixture is stirred at rt for 48 h. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue is vacuum distilled at 170° C. to give 1.24 g of the product 448.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. distillationdistilled at 170° C.

Sources & evidence

ORD record
ord-3b96a48cc5554c38937449e8fff31ec8
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741493B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes