Diethyl Ether → HCID 53646573, compound

HRID 2399340Notes

Reaction equation

HRID 2399340 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C@@H:17]1[O:28][C@:18]1([C:24]([O:26]C)=[O:25])[CH2:19][C:20]([O:22]C)=[O:21].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[OH-].[K+].CCOCC>OS(O)(=O)=O.O.CO.CCOCC>[C:24]([C@:18]1([OH:28])[C@@H:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[O:22][C:20](=[O:21])[CH2:19]1)([OH:26])=[O:25]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6628DiazaldHCID 14797Potassium HydroxideHCID 57113502HCID 57113502, compound

Product 1

HCID 53646573HCID 53646573, compoundYield 67.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

±(3R*,4S*) Methyl 12-(2,4-dichlorophenyl)-3,4-epoxy-3-methoxycarbonyldodecanoate (314 mg, 0.728 mmol) was heated at reflux in aqueous H2SO4 (7.5M) for 3.5 h. The solution was diluted with water, and extracted with ether. The extracts were washed with water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under vacuum. Diazomethane, generated from diazald (450 mg, 2.10 mmol) and aqueous KOH (10.7M), was passed in a stream of ether saturated nitrogen through a solution of the crude acid in 10% methanol/ether (10 ml) until a yellow colouration was seen in the reaction flask. Excess diazomethane was quenched with acetic acid, then the solvent removed under vacuum. The residue was purified by chromatography on silica gel (50-80% ether/petroleum ether 40°-60° C.) to give the title compound (198 mg, 65%) as an oil.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water, saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under vacuum
  5. customExcess diazomethane was quenched with acetic acid
  6. customthe solvent removed under vacuum
  7. customThe residue was purified by chromatography on silica gel (50-80% ether/petroleum ether 40°-60° C.)

Sources & evidence

ORD record
ord-603d99b0961241eda5c90a4ca0f98ee0
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

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