Tetrahydrofuran → HCID 121360802, compound

HRID 531402Notes

Reaction equation

HRID 531402 reaction equation
[CH2:1]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1)[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([O:10][CH3:11])[CH:4]=1.C1COCC1.[N:26]#[C:27]Br.[CH2:29]([N:31](CC)CC)C>>[O:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][C:27]#[N:26])=[C:5]([O:10][CH3:11])[CH:4]=2)=[CH:13][C:14]=1[O:19][CH3:20])[C:29]#[N:31]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 148038254,4'-(Ethane-1,2-diyl)bis(2-methoxyphenol)

Product 1

HCID 121360802HCID 121360802, compound

Conditions

Temperature
-20 °C

Procedure

A round bottom flask was charged with 1.05 g (3.8 mmol) of 4,4′-(ethane-1,2-diyl)bis(2-methoxyphenol), THF (40 mL), and CNBr (1.06 g, 10 mmol). The flask was cooled to −20° C. and triethylamine (1.16 mL) was added dropwise. A tan solid immediately precipitated from solution. The mixture was stirred at −20° C. for 10 min and was then removed from the cold bath and allowed to spontaneously warm. After stirring for an additional 30 min, the mixture was filtered on a medium glass-frit and the solid washed with water (3×20 mL) and then air dried to yield 0.71 g of crude product. Evaporation of the filtrate followed by water and ether washes vielded an additional 0.22 g of product for a total of 0.93 g (76%). Recrystallization from hot THF yielded 625 mg of tan needles. 1H NMR (DMSO-d6) δ 7.42 (d, 2H, J=8 Hz), 7.18 (s, 2H), 6.91 (d, 2H, J=8 Hz), 3.88 (s, 3H, OMe), 2.91 (s, 2H, CH2). Anal. Calcd for C18H16O4N2: C, 66.86; H, 4.97. Found: C, 66.67; H 4.96.

Workup

  1. customA tan solid immediately precipitated from solution
  2. customwas then removed from the cold bath
  3. temperatureto spontaneously warm
  4. stirringAfter stirring for an additional 30 min
  5. filtrationthe mixture was filtered on a medium glass-frit
  6. washthe solid washed with water (3×20 mL)
  7. customair dried
  8. customto yield 0.71 g of crude product
  9. customEvaporation of the filtrate
  10. customRecrystallization from hot THF

Sources & evidence

ORD record
ord-2bf7413230324e728a0c59f6169b01ed
Source dataset
uspto-grants-2016_05
Patent number
US09353219B1

Reaction notes

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