Propylethinylcarbinol → (1-Ethynylbutoxy)acetic Acid Ethyl Ester

HRID 2053613Notes

Reaction equation

HRID 2053613 reaction equation
[CH:1]#[C:2][CH:3]([OH:7])[CH2:4][CH2:5][CH3:6].[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][O:7][CH:3]([C:2]#[CH:1])[CH2:4][CH2:5][CH3:6])[CH3:15]

Participants

6

Reactant 2

HCID 7746PropylethinylcarbinolHCID 12192Ethyl diazoacetate

Product 1

HCID 86140139(1-Ethynylbutoxy)acetic Acid Ethyl EsterYield 54.3%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 1-hexyn-3-ol (981 mg, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.0 mL, 9.0 mmol). The reaction mixture is stirred at rt for 6 h. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel: elution with EtOAc:heptane (25:75) gives 900 mg of the product 446. 1H NMR (CDCl3) δ 4.35-4.10 (m, 5H), 2.43 (s, 1H), 1.90-1.65 (m, 2H), 1.65-1.40 (m, 2H), 1.40-1.20 (m, 3H), 0.95 (t, 3H)

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe residue purified by chromatography on silica gel
  4. washelution with EtOAc:heptane (25:75)

Sources & evidence

ORD record
ord-55afeda684e14f9a9932a9f2686bbdb9
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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