Potassium Iodide → HCID 19916955, compound

HRID 1464798Notes

Reaction equation

HRID 1464798 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[CH2:11][O:12][CH2:13][C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:6]=[CH:7][CH:8]=1.ClC1C=CC=C(C(OO)=[O:27])C=1.[Li].[H-].Cl.[CH2:33]([NH:35][CH2:36]/[CH:37]=[CH:38]/[C:39]#[C:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH3:34].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C1C=CC=CC=1.C(OCC)C.CN(C)C=O.O>[CH2:33]([N:35]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH:10]([OH:27])[CH2:11][O:12][CH2:13][C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:4]=1)[CH2:36]/[CH:37]=[CH:38]/[C:39]#[C:40][C:41]([CH3:43])([CH3:42])[CH3:44])[CH3:34]

Participants

12

Reactant 7

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 166653HydrideHCID 3028194LithiumHCID 19916933HCID 19916933, compoundHCID 19917114(E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

Product 1

HCID 19916955HCID 19916955, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

62 mg of 3(3-chlromethylphenyl)-1-(3-thienylmethoxy)-2-propanol [synthesized by the epoxidation reaction of (E)-3-[3-(3-chloromethylphenyl)-2-propenyloxymethyl]thiophene with m-chloroperbenzoic acid in benzene, followed by the reduction with lithium aluminun hydride in ethyl ether] was dissolved in 1 ml of dimethylformamide, and 47 mg of (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride, 49 mg of potassium carbonate and 3 mg of potassium iodide were added. The mixture was stirred overnight at room temperature, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by medium-pressure liquid chromatography [silica gel column, hexane/ ethyl acetate=5/1→4/1] to give 61 mg of the captioned compound as a colorless oil.

Workup

  1. customThe organic layer separated
  2. customthe product was purified by medium-pressure liquid chromatography [silica gel column, hexane/ ethyl acetate=5/1→4/1]

Sources & evidence

ORD record
ord-d72ed3b328ea41fb89c4d77071377e72
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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