Dichloromethane → HCID 23349565, compound

HRID 2058134Notes

Reaction equation

HRID 2058134 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12]/[C:13](=[CH:21]\[CH2:22][CH2:23][C:24](=[CH2:27])[CH:25]=[CH2:26])/[CH2:14][CH2:15][C:16]([O:18]CC)=[O:17].C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:9][CH:21]([C:13]1([CH3:12])[CH2:14][CH2:15][C:16](=[O:18])[O:17]1)[CH2:22][CH2:23][C:24](=[CH2:27])[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 10987849HCID 10987849, compound

Product 1

HCID 23349565HCID 23349565, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (36 g, 0.175 M) is added in five portions to a mixture of ethyl 4-methyl-8-methylene-(E)-4,9-decadienoate (40 g, 0.18 M) and methylene chloride (1 l), at -8° C. under nitrogen and the resulting mixture is stirred for two hours. The precipitate is filtered and the filtrate dried in vacuo to give crude ethyl 4-methyl-8-methylene-4,5-oxido-9-decenoate. This material is dissolved in methanol (200 ml) and the resulting solution is treated with saturated potassium carbonate solution (50 ml) and water (50 ml) and stirred overnight. Most of the methanol is removed in vacuo, the residue is cooled to 0° C. and slowly treated with conc. hydrochloric acid (150 ml). The resulting mixture is extracted with ether (3×350 ml). The combined organic layers are dried (Na2SO4), the solvent is removed in vacuo, and the residue (52 g) is purified by column chromatography on silica gel (400 g) with ether-petroleum ether (4:1) to give 2-(1-hydroxy-4-methylene-5-hexenyl)-2-methyl-5-oxo-tetrahydrofuran as a colorless liquid (22 g, 58%).

Workup

  1. filtrationThe precipitate is filtered
  2. customthe filtrate dried in vacuo
  3. customto give crude ethyl 4-methyl-8-methylene-4,5-oxido-9-decenoate
  4. stirringstirred overnight
  5. customMost of the methanol is removed in vacuo
  6. additionslowly treated with conc. hydrochloric acid (150 ml)
  7. extractionThe resulting mixture is extracted with ether (3×350 ml)
  8. dry with materialThe combined organic layers are dried (Na2SO4)
  9. customthe solvent is removed in vacuo
  10. customthe residue (52 g) is purified by column chromatography on silica gel (400 g) with ether-petroleum ether (4:1)

Sources & evidence

ORD record
ord-483e41ab87a049718316c8983cd5b1c6
Source dataset
uspto-grants-1980_07
Patent number
US04215048

Reaction notes

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