Bromomethyl 4-methoxyphenyl ketone → HCID 21498933, compound

HRID 1730078Notes

Reaction equation

HRID 1730078 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1.CN(C)[CH:15]=[O:16].N1(C2[CH2:28][CH2:27][S:26][CH2:25][CH:24]=2)CCCC1>O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][CH:24]2[C:15](=[O:16])[CH2:28][CH2:27][S:26][CH2:25]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 6228Dimethylformamide2×HCID 132874681-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

Product 1

HCID 21498933HCID 21498933, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 23.7 g (0.10 mole) of p-methoxyphenacyl bromide in 50 ml. of dimethylformamide is added dropwise under nitrogen to a cold stirred solution of 16.9 g (0.10 mole) of 5,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran [Example 1 (a)] and 10 ml. of dimethylformamide. After 5 hours the reaction mixture is diluted with water and extracted with chloroform. The chloroform solution is washed with water, dried over magnesium sulfate, and concentrated to an oil which solidifies. The solid is suspended in methanol. The mixture is filtered and the filtrate is concentrated to a solid. The resulting solid is recrystallized from methanol and then from acetic acid to give off-white crystals of 3-(4-methoxyphenacyl)-2,3,5,6-tetrahydrothiopyran-4-one, m.p. 123° to 125°C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to an oil which
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated to a solid
  7. customThe resulting solid is recrystallized from methanol

Sources & evidence

ORD record
ord-9b7e7403d3b548ceb79f6d63440271da
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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