Dichloromethane → HCID 519056, compound

HRID 2387727Notes

Reaction equation

HRID 2387727 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8]1([CH2:14][C:15](Cl)=[O:16])[CH:13]=CC=C[CH:9]=1.Cl[CH2:19]Cl.[CH3:21][C:22]([CH3:26])=[CH:23][CH2:24][OH:25]>O>[C:22]1([CH2:23][C:24]([O:16][CH2:15][CH:14]=[C:8]([CH3:13])[CH3:9])=[O:25])[CH:26]=[CH:7][CH:6]=[CH:19][CH:21]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 111733-Methyl-2-buten-1-OL

Product 1

HCID 519056HCID 519056, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (9.7 ml) and phenylacetyl chloride (7.67 ml) were added to a dichloromethane solution (50 ml) of 3-methyl-2-buten-1-ol (5 g), while the solution was stirred under cooling on ice. The obtained mixture was stirred under cooling on ice for 3 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with dichloromethane. The obtained organic layer was dried over magnesium sulfate, and was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=1:0 to 19:1), so as to obtain the title compound (11.5 g).

Workup

  1. temperatureunder cooling on ice
  2. stirringThe obtained mixture was stirred
  3. temperatureunder cooling on ice for 3 hours
  4. extractionthe obtained mixture was then extracted with dichloromethane
  5. dry with materialThe obtained organic layer was dried over magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=1:0 to 19:1)

Sources & evidence

ORD record
ord-793bd94fc1b94e1f888ac1b8b27e58ab
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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