Perchloric Acid → Methyl 4-acetyl-4-tert-butoxycarbonyl-3-formyl-6-nonynoate

HRID 46545Notes

Reaction equation

[C:1]([C:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:16][C:17]#[C:18][CH2:19][CH3:20])[CH:5]([CH:11](OC)[O:12]C)[CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:1]([C:4]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])([CH2:16][C:17]#[C:18][CH2:19][CH3:20])[CH:5]([CH:11]=[O:12])[CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 28 °C

Procedure

Methyl 4-acetyl-4-tert-butoxycarbonyl-3-dimethoxymethyl-6-nonynoate (546 mg) is dissolved in 30 ml of tetrahydrofuran, and 25 ml of 1.5% aqueous solution of perchloric acid is added to the solution. The mixture is stirred at 28° C. for 12 hours. Subsequently the reaction mixture is neutralized with sodium bicarbonate and concentrated in a vacuum. The residue is extracted with ethyl acetate. The extract is dried and then concentrated to give methyl 4-acetyl-4-tert-butoxycarbonyl-3-formyl-6-nonynoate (compound (7), R1 =t-Bu, R2 =CH3) in a yield of 98.0%.

Workup

concentrationconcentrated in a vacuum
extractionThe residue is extracted with ethyl acetate
customThe extract is dried
concentrationconcentrated

Sources & evidence

ORD record: ord-58fe40bbcaba4ba9b27f2b538c1ef89c
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04173707

Reaction notes

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