1,2-Dibromoethane → HCID 15078312, compound

HRID 1196700Notes

Reaction equation

HRID 1196700 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH:5][CH:6]([CH3:39])[CH2:7][S:8]([C:11]1[CH:12]=[C:13]([C@H:22]2[CH2:26][CH2:25][C@H:24]([C:27]3[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=3)[O:23]2)[CH:14]=[C:15]([OH:21])[C:16]=1[O:17][CH2:18][CH2:19][CH3:20])(=[O:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:5][CH:6]([CH3:39])[CH2:7][S:8]([C:11]1[CH:12]=[C:13]([C@H:22]2[CH2:26][CH2:25][C@H:24]([C:27]3[CH:28]=[C:29]([O:37][CH3:38])[C:30]([O:35][CH3:36])=[C:31]([O:33][CH3:34])[CH:32]=3)[O:23]2)[CH:14]=[C:15]([O:21][CH2:3][CH2:2][Br:1])[C:16]=1[O:17][CH2:18][CH2:19][CH3:20])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 15078298HCID 15078298, compound

Product 1

HCID 15078312HCID 15078312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1,2-Dibromoethane (1.12 mL, 13 mmol) was added to a solution of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (331 mg, 0.65 mmol) (Example 18) in DMF (5 mL) containing potassium carbonate (550 mg, 3.9 mmol). The reaction mixture was heated with stirring at 70° C. for 7 h and, cooled, and partitioned between ethyl ether and water. The ethereal layer was separated and the aqueous layer was re-extracted twice with ether. The organic extracts were combined, dried, and evaporated to dryness. The product was purified by flash column chromatography on silica gel using hexane-ethyl acetate (2:1, v/v) as the eluant: Rf 0.42 (hexane-ethyl acetate; 1:2, v/v); NMR (CDCl3) δ 1.06 (t, CH2CH2CH3). 1.25 (d, CH2CHOHCH3), 1.90 (m, CH2CH2CH3), 3.74 (t, CH2CH2Br), 3.83 (s, OCH3), 3.88 (s, 2 OCH3), 5.16-5.28 (m, H-2 & H-5), 6.62 (s, 2 H, C5ArH), 7.28 and 7.54 (2 d, 2 H, C2ArH).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled
  3. custompartitioned between ethyl ether and water
  4. customThe ethereal layer was separated
  5. extractionthe aqueous layer was re-extracted twice with ether
  6. customdried
  7. customevaporated to dryness
  8. customThe product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ad1d2b1e869d49c186c4f5001d9cbb68
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

Loading…