Hydrochloric Acid → HCID 117701566, compound

HRID 1507448Notes

Reaction equation

HRID 1507448 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH:19]=[O:20])=[C:17]2[C:12]([C:13](=[O:32])[C:14]([CH3:31])=[C:15]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:23][CH2:22]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:33]1([Mg]Br)[CH2:35][CH2:34]1.Cl.O>O1CCCC1>[CH2:1]([O:8][C:9]1[C:18]([CH:19]([CH:33]2[CH2:35][CH2:34]2)[OH:20])=[C:17]2[C:12]([C:13](=[O:32])[C:14]([CH3:31])=[C:15]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:23][CH2:22]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 117701716HCID 117701716, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 117701566HCID 117701566, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 7-(benzyloxy)-3-methyl-4-oxo-2-(1-propanoylpiperidin-4-yl)-4H-chromene-8-carbaldehyde (200 mg, 0.46 mmol) obtained in Example 34-2 in tetrahydrofuran (6 mL), a 1 N solution of cyclopropyl magnesium bromide in tetrahydrofuran (1.5 mL, 1.50 mmol) was added dropwise at −30° C., and the mixture was gradually heated to 0° C. over 45 minutes and then stirred at 0° C. for 2 hours. A 1 N aqueous hydrochloric acid solution (5 mL) was added dropwise to the reaction solution, and then water was added to the mixture, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=60/40→0/100) to obtain 159 mg of the title compound (yield: 68%) as an oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=60/40→0/100)

Sources & evidence

ORD record
ord-19f931d9fe1b41218cd3ba5466a62acf
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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