Tetrahydrofuran → HCID 15482433, compound

HRID 600127Notes

Reaction equation

HRID 600127 reaction equation
CN1C(=O)N(C)[CH2:5][CH2:4][CH2:3]1.[C:10]([Li])#[C:11][CH2:12][CH2:13][CH3:14].BrCC1C(CBr)=C(CCC)[C:29]2[C:20](=[CH:21][C:22]3[C:27]([CH:28]=2)=[C:26]([CH2:37][CH2:38][CH3:39])[C:25]([CH2:40][CH2:41][CH3:42])=[C:24]([CH2:43][CH2:44][CH3:45])[C:23]=3[CH2:46][CH2:47][CH3:48])C=1CCC.[CH2:52]1[CH2:56]O[CH2:54][CH2:53]1>>[CH2:4]([C:5]1[C:13]([CH2:12][C:11]#[C:10][CH2:24][CH2:23][CH3:46])=[C:14]([CH2:26][CH2:25][CH3:40])[C:48]2[C:47](=[CH:46][C:23]3[C:22]([CH:21]=2)=[C:27]([CH2:28][CH2:29][CH3:20])[C:26]([CH2:37][CH2:38][CH3:39])=[C:25]([CH2:40][CH2:41][CH3:42])[C:24]=3[CH2:43][CH2:44][CH3:45])[C:29]=1[CH2:20][CH2:21][CH3:22])[C:3]#[C:54][CH2:53][CH2:52][CH3:56]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 15482432HCID 15482432, compoundHCID 178506795HCID 178506795, compound

Product 1

HCID 15482433HCID 15482433, compoundYield 87%

Procedure

2,3-Bis(bromomethyl)-1,4,5,6,7,8-hexapropylanthracene obtained in REFERENCE EXAMPLE 4 was employed. N,N′-Dimethylproyleneurea (DMPU) and 1-pentynyl lithium were added to the solution of 2,3-bis(bromomethyl)-1,4,5,6,7,8-hexapropylanthracene in THF. The reaction mixture was stirred at room temperature for an hour. The reaction was quenched with 3N Hydrochloric acid. Next, the reaction mixture was extracted with ether. After washing with sodium hydrogencarbonate aqueous solution and brine, the extract was dried over anhydrous magnesium sulfate. After the extract was concentrated under reduced pressure, column chromatography with silica gel as the packing material was performed using hexane. Recrystallization from methanol gave 6.372 g (12.338 mmols) of the title compound as a yellow solid. The isolation yield was 87%.

Workup

  1. customThe reaction was quenched with 3N Hydrochloric acid
  2. extractionNext, the reaction mixture was extracted with ether
  3. washAfter washing with sodium hydrogencarbonate aqueous solution and brine
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. concentrationAfter the extract was concentrated under reduced pressure, column chromatography with silica gel as the packing material
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-44f6e08ebd10451c8d7ea970dde422f6
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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