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

HRID 1732431
Notes
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Reaction equation

HRID 1732431 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 180
Acetone
Solvent
2×

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 (8), 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-612fb524cbff41f38479e6c85551a300
Source dataset
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04237308

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes