1,3-Propanediol → HCID 69069982, compound

HRID 1987832Notes

Reaction equation

HRID 1987832 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[N+](=[C:8]1[CH2:12][CH2:11][O:10][C:9]1=[O:13])=[N-]>ClCCl.C(OCC)C.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[OH:4][CH2:3][CH2:2][CH2:1][O:5][CH:8]1[CH2:12][CH2:11][O:10][C:9]1=[O:13]

Participants

6

Reactant 2

HCID 104421,3-PropanediolHCID 12208388HCID 12208388, compound2×

Product 1

HCID 69069982HCID 69069982, compound

Reagents, catalysts & solvents 3

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Propane-1,3-diol (0.050 g, 0.657 mmol) was dissolved in dichloromethane (6.5 mL) and treated with rhodium (II) acetate (3 mg) then solution was heated to reflux. One third of a solution (ca. 2 mL) of 3-diazodihydrofuran-2(3H)-one (0.283 g, 0.986 mmol) dissolved in a mixture of dichloromethane (3 mL) and diethyl ether (2.5 mL) was added dropwise to the hot solution then the solution was heated at reflux for 30 minutes. The solution of 3-diazodihydrofuran-2(3H)-one was added in two portions (ca. 2 mL each) to the refluxing mixture in a similar manner. The reaction was cooled to ambient temperature and concentrated in vacuo. The crude oil was chromatographed on silica gel eluting with ethyl acetate/hexanes (2:1). 3-(3-Hydroxypropoxy)dihydrofuran-2(3H)-one was recovered as a colorless oil (47 mg, 45%).

Workup

  1. temperaturesolution was heated to reflux
  2. additionwas added dropwise to the hot solution
  3. temperaturethe solution was heated
  4. temperatureat reflux for 30 minutes
  5. concentrationconcentrated in vacuo
  6. customThe crude oil was chromatographed on silica gel eluting with ethyl acetate/hexanes (2:1)
  7. custom3-(3-Hydroxypropoxy)dihydrofuran-2(3H)-one was recovered as a colorless oil (47 mg, 45%)

Sources & evidence

ORD record
ord-8e70926214a247e69bb290286a7637fb
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

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