Potassium Iodide → Methyl 4-acetyl-4-tert-butoxycarbonyl-3-dimethoxymethyl-6-nonynoate

HRID 261628Notes

Reaction equation

HRID 261628 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:9]([O:13][C:14]([CH:16]([C:28](=[O:30])[CH3:29])[CH:17]([CH:23]([O:26][CH3:27])[O:24][CH3:25])[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:15])([CH3:12])([CH3:11])[CH3:10].[C:31](Br)#[C:32][CH2:33][CH2:34][CH3:35]>CC(C)=O>[C:28]([C:16]([C:14]([O:13][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:15])([CH2:31][C:32]#[C:33][CH2:34][CH3:35])[CH:17]([CH:23]([O:24][CH3:25])[O:26][CH3:27])[CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 117687131-Bromopent-1-yneHCID 20396638Methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate

Product 1

HCID 54174852Methyl 4-acetyl-4-tert-butoxycarbonyl-3-dimethoxymethyl-6-nonynoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A 1.38 g quantity of potassium carbonate and 308 mg of potassium iodide are placed into a reactor. Acetone (30 ml) and a solution of 450 mg of methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate in 10 ml of acetone are further placed into the reactor. Subsequently 270 mg of pentynyl bromide is added to the mixture. The resulting mixture is stirred at room temperature for one hour and thereafter refluxed at 70° C. for 13 hours. On completion of the reaction, the mixture is cooled to room temperature, and the solids are separated off. The product is concentrated in a vacuum, and the residue purified by a silica gel column, giving methyl 4-acetyl-4-tert-butoxycarbonyl-3-dimethoxymethyl-6-nonynoate (compound (7), R1 =t-Bu, R2 =R3 =CH3) in a yield of 91%.

Workup

  1. temperaturerefluxed at 70° C. for 13 hours
  2. customOn completion of the reaction
  3. temperaturethe mixture is cooled to room temperature
  4. customthe solids are separated off
  5. concentrationThe product is concentrated in a vacuum
  6. customthe residue purified by a silica gel column

Sources & evidence

ORD record
ord-952e84970e8046fdaab0183d6b33937c
Source dataset
uspto-grants-1979_08
Patent number
US04166188

Reaction notes

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