Tetrahydrofurfuryl alcohol → (Tetrahydrofuran-2-ylmethoxy)acetic Ethyl Ester

HRID 18833

Reaction equation

HRID 18833 reaction equation
[CH2:1]([OH:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]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][O:7][CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][O:6]1)[CH3:15]

Participants

6

Reactant 2

HCID 7360Tetrahydrofurfuryl alcoholHCID 12192Ethyl diazoacetate

Product 1

HCID 43119675(Tetrahydrofuran-2-ylmethoxy)acetic Ethyl EsterYield 60.2%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of tetrahydrofurfuryl alcohol (1.02 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at rt for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 130° C. to give 1.02 g of the product 477. 1H NMR (CDCl3) δ 4.11 (q, 2H), 4.10 (s, 2H), 3.93 (m, 1H), 3.72 (m, 1H), 3.61 (m, 1H), 3.44 (m, 2H), 1.95-1.75 (m, 3H), 1.61-1.53 (m, 1H), 1.20 (t, 3H).

Workup

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 130° C.

Sources & evidence

ORD record
ord-204f5de948154c3eb146710bb643fd31
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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