Diazomethane → 3-[3-hydroxy-1,9-dimethoxy-5,9-dimethyl-(E)-decenylidene]-4-butyrolactone

HRID 67127Notes

Reaction equation

HRID 67127 reaction equation
[N+](=[CH2:3])=[N-].[CH3:4][O:5][C:6]([CH3:25])([CH3:24])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:23])[CH2:11][CH:12]([OH:22])[CH2:13][C:14]([CH:16]1[CH2:21][O:20][C:18](=[O:19])[CH2:17]1)=[O:15]>CCOCC>[OH:22]/[C:12](/[CH2:11][CH:10]([CH3:23])[CH2:9][CH2:8][CH2:7][C:6]([O:5][CH3:4])([CH3:24])[CH3:25])=[CH:13]/[C:14](=[C:16]1[CH2:21][O:20][C:18](=[O:19])[CH2:17]1)[O:15][CH3:3]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 20528523HCID 20528523, compound

Product 1

HCID 867385333-[3-hydroxy-1,9-dimethoxy-5,9-dimethyl-(E)-decenylidene]-4-butyrolactoneYield 63.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An etherealdiazomethane solution containing 0.04 moles of diazomethane is added to a solution of 2.0 g (0.006 moles) of 3-(9-methoxy-3-hydroxy-5,9-dimethyl-decanoyl)-4-butyrolactone in 5 ml of dry ether, and the reaction mixture is allowed to stand at room temperature for 4 hours. The solvent is distilled off in vacuo, the residue is taken up with ether, and the solution is filtered through a short column filled with Kieselgel 60 adsorbent. Ether is removed from the effluent to obtain 1.2 g (63.2%) of the aimed compound as a pale yellow oil; Rf =0.62 (developed with a 10:0.4 mixture of benzene and methanol).

Workup

  1. distillationThe solvent is distilled off in vacuo
  2. filtrationthe solution is filtered through a short column
  3. additionfilled with Kieselgel 60 adsorbent
  4. customEther is removed from the effluent

Sources & evidence

ORD record
ord-ce7495193084499baedc71ddda582255
Source dataset
uspto-grants-1982_08
Patent number
US04344959

Reaction notes

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