Water → HCID 19792470, compound

HRID 1655505Notes

Reaction equation

HRID 1655505 reaction equation
[Mg].[CH:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]Br)=[CH:4][CH:3]=1.[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24])([O:13][CH3:14])=[O:12].O.[CH2:27](OCC)C>>[O:24]=[C:23]([CH2:27][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl Ether3×HCID 7666Phenethyl bromideHCID 544219Methyl 10-chloro-10-oxodecanoateHCID 5462224Magnesium

Product 1

HCID 19792470HCID 19792470, compound

Procedure

To a suspension of magnesium (turnings, 17.1 g) in ethyl ether (300 ml), a solution of β-phenethyl bromide (140 g, 0.7 mol) in ethyl ether was added dropwise under mild reflux with vigorous stirring under nitrogen, and stirring was continued for 1 h under reflux. After cooling, the mixture (Grignard reagent) was added dropwise to a solution of 9-carbomethoxynonanoyl chloride (150.1 g, 0.64 mol) in ethyl ether (500 ml) at -50°~-30° C. The mixture was allowed to warm to room temperature, stirred for 2 h at the same temperature and poured into H2O (500 ml). The organic layer was separated, washed with H2O, dried over anhydrous MgSO4 and evaporated in vacuo. The residue (203 g) was chromatographed on silica gel (Wako Gel C-200, manufactured by Wako Pure Chemical Industries, Ltd.) with n-hexane/ethyl acetate (4:1) as eluent to afford the title compound as a colorless oil; yield: 99.7 g.

Workup

  1. temperatureunder mild reflux
  2. stirringstirring
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. stirringstirred for 2 h at the same temperature
  6. customThe organic layer was separated
  7. washwashed with H2O
  8. dry with materialdried over anhydrous MgSO4
  9. customevaporated in vacuo
  10. customThe residue (203 g) was chromatographed on silica gel (Wako Gel C-200, manufactured by Wako Pure Chemical Industries, Ltd.) with n-hexane/ethyl acetate (4:1) as eluent

Sources & evidence

ORD record
ord-dc4145a4d32c46eb8350f435ff882080
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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